The Questions You Need to Ask When Building a Team

Building a team is one of the hardest things to do, and yet it’s so crucial to creating a sustaining, successful business with happy employees. We’ve heard Brad share his basic philosophy on this a few times, and the value of it cannot be overstated: Work with people you like.

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While that’s a simple foundation to start from, there are also some key questions to ask and qualities to look for when you’re building up your team. One of the best things about WDS is the fact that it has so many amazing team members, many of which have backstories that, from the outside, may not make them look like the obvious best fit for a web development agency. The reason that we have such an eclectic crew, though, is because the questions that our folks ask themselves (and of prospective team members) when expanding are often questions that cannot be answered by reading a resume.

Today, a few WDS leaders share their insight on how to effectively build a skilled, capable, and downright rad team. All three of our Project Managers, Cristina Cannon, Melissa Hoppe, and Jaimie Olmstead, chipped in, as well as our VP of Operations, Dre Armeda, and the founder of Maintainn, Shayne Sanderson. Each person comes at this from a different angle, not only because of their own personal perspective and past professional experience, but because the various roles they have at WDS can vary wildly, so the answers are all a little different, and may help you next time you’re looking to expand your recent venture.

What are the questions you ask yourself when developing a team?

SHAYNE: I always look for people smarter than myself. Having a diverse team is important as well, especially on the support side of things. We encounter many various issues where a diverse team plays a big role. In short, I look for experienced developers that are reliable, trustworthy and capable of just about anything I could throw their way.

JAIMIE: List out specific skills/characteristics that current team members have (and even skills they don’t possess that we may need for upcoming projects) and check off the items each team member possesses. Keep this updated as your team develops and you’ll see areas of opportunity emerge for new candidates. You want a well-rounded team to be able to move easily from one project to the next.

DRE: Are we ready to augment our team with another resource? Does the work that needs to be done justify a new resource? Are we financially able to take on the resource? What is the goal of the resource? What are the overall benefit/risks?

What are the questions you ask potential team members to figure out whether or not they’ll be a good fit?

DRE: There is some variance here dependent on the position and level of seniority. I ask skillset questions AND experience questions to gauge whether they are really worth chatting with in-depth. I then get into decision-making, communications, and conflict resolution scenarios and questions.

CRISTINA: I ask them what the expertise, experience and skill levels are, and have them provide examples to confirm these are true.

MELISSA: Basically the same as Cristina–I make sure I know what their specific skill set is and confirm that it holds true.

JAIMIE: What are your strongest skill sets? What are some examples of this? What will you bring to our team that we may not currently have? If I were to ask (insert reference) why they enjoyed working with you, what would they tell me? Tell me about your most challenging project. What made it challenging and how did you adapt? Have you worked in a team environment before or just freelance? What’s your experience with Project Managers and how do you prefer to be managed? Tell me about a time when you’ve helped out a coworker. If you saw a team member struggling to complete a task, but you are loaded up with work for a tight deadline what would you do? Tell me about a time when you were overloaded with work in a time crunch with a client. Tell me about a difficult client, how did you/or your team manage them?

What are the qualities you look for when looking to add to an existing team?

MELISSA: Make sure they will fit in well with the current team. Not only in the work aspect, but also personality wise. (We’re weird, so they have to be weird too). Also make sure that their work is up to par with the current existing team and are willing to learn. Also need to be willing to do things a different way than they are used to. Flexibility is a must.

SHAYNE: Personality is a big one. Even if all of the skills match up, the person needs to fit into our “group.” That’s not to say we don’t all have our differences, but we work closely each day and that’s an important piece of our dynamic. Work methods can be adjusted over time to meet needs, etc but the person definitely needs to “fit” with us on a more personal level in my opinion as that can make a huge difference (good or bad).

DRE: Communication, confidence, problem-solving skills, passion, and learnability lead the pack!

What do you feel is an overlooked aspect of team building?

JAIMIE: Evaluating what type of personalities you’re bringing onto a team with management styles. Project Managers may have the same job objectives, but go about them in different ways. Same for leads. Ask about this during the interviewing process. How do you like to be managed? Everyone learns in different ways (visual, audible, hands on) and we can help them by determining that and working with them from the start.

DRE: The notion that people grow and mature in their role. Good leadership enables growth and progression. You should always be thinking about your team members growth and have a good understanding of where they want their growth to go.

CRISTINA: Confidence/comfort level! Adding a new person to an existing team can be difficult. There is already a level of confidence among team members. I feel like a new developer or designer needs to come in and possess a level of confidence in their work so that the existing team members are comfortable.

MELISSA: Confidence in their work is definitely a big one. Coming into an already existing team who have worked together for a while can be intimidating. As a whole, WDS is great at accepting new devs/designers and teaching them as much as they can. We just need to make sure that they feel like they aren’t ‘less than’ anyone else.

SHAYNE: In my opinion, an overlooked area could easily be “personality.” Sometimes building teams is from necessity and if you’re quick to just get a warm body in place it could prove to be a bad decision over time. Personality could be how they get along with the other team members, how they like to work, how they like (or dislike) to be managed, etc., and I think it’s an important piece that can be overlooked when things are rushed.

What’s a common mistake that you have seen other people make (or you have made yourself) when adding new members to a team? 

MELISSA: Communication. In my experience, there have been times that projects/tasks have gotten mixed up/lost in communication. Making sure there is a clear communication is super important.

JAIMIE: During the interviewing phase, one mistake I’ve made in the past and have learned from, and have coached others on how to avoid is asking leading questions. Often to not put themselves or the candidate in an uncomfortable place we ask questions that will lead the candidate to the answers we want to hear.

For example, “Are you comfortable with asking for help?” Most candidates will, of course, identify this as a necessary skill and say “YES, OF COURSE!” Instead, ask an open-ended question that allows the candidate to bring what they feel is relevant information surrounding the problem (which in this case, is feeling comfortable asking for help). A better way to frame it is by saying, “Tell me about a time when you feeling in over your head,” and go from there.

CRISTINA: Not communicating expectations. You have to make sure that new team members know what the expectations are. You can do this by having a formal training in place so that during that timeframe expectations are set for the new team member.

SHAYNE: Growing too quickly. It’s easy to see your workload increase and want to hire everyone you can think of! I think growing slowly is best and although tough at times (with heavy workloads), it’s the smarter way to approach things. I’d prefer to have a smaller/busier team than a large team that I am not certain I could sustain long-term (if projects go away, etc)

DRE: Not pulling the trigger. Paralysis through analysis. Hiring too quickly is a risk indeed, but not hiring quick enough is just as risky if not worse. So pace of team growth can be problematic.

Defining roles and expectations are the key to building a successful event. Measure effectiveness and guide to growth. If you’re not measuring, there’s no way to develop your team, there’s no way to understand if the team is working effectively towards the team goals and mission.

What are other ways you assess whether someone will be a good fit (aside from direct questions and answers)? Are there are other “tells” about how someone is going to engage with your existing team?

SHAYNE: I listen to how they talk. I listen to how they describe previous employers. I listen to how they describe themselves, work ethics, experience. You can tell a lot by how someone says things opposed to what they say.

For example, I could tell you all about how I could build a rocket that would fly to different galaxies, but you could tell pretty quickly by how I explained it that I was full of shit. I’m pretty good at reading people so I pay close attention on “how” they talk about themselves, previous employers, their skills, and more.

CRISTINA: Sometimes a new team member has all the experience and skills needed, but their personality or something outside of your control keeps them from really engaging with the team the way they need to, and sometimes they just are not the right fit for the company or position.

MELISSA: As someone who has spent a lot of time in customer service, you begin to notice a lot of tells or red flag when talking with someone. When someone becomes defensive, that’s a huge red flag. “I see there’s an error here…” “YEAH, BUT…” No good. Also, what Cristina said about personalities. Sometimes certain personalities won’t fit either.

JAIMIE: Initial communication during interviewing process–are they good communicators? Also, negativity or someone who doesn’t have a can do attitude. We face challenges DAILY and the worst type of person who can quickly sour an entire team is someone who will complain and groan about every challenge.

Ask questions related to this during interviewing process, “As I’m sure you’ve experienced, we’ve had some challenging clients/projects. How do you handle difficult requests that may cause you to switch gears completely? Tell me a about a time you’ve had to do this.” If the entire answer the candidate gives is essentially complaining about the client/project, and not presenting how they came to a solution, chances are they’re a Negative Nancy and I’d avoid bringing them on.

Wondering what else to ask your future team members? Have other questions about vetting? Give us a shout in the comments!


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