#ManagementHeroes with Charla Session-Reed – Senior Director of Marketing at ShipStation

Captaining a Marketing Team: How a Senior Director of Marketing facilitates learning through one-on-one meetings and career conversations.

Shipstation Management

When Charla Session-Reed joined Shipstation in 2015, there were only 53 people at the company. Fast-forward to 2020, and they’ve hired over 300 employees – 35 of which belong to the marketing team.

This rapid growth presented Charla with the opportunity to do one of the things that she loves the most: coaching, mentoring, and helping her teammates grow.

“I just love the people management – and building the team,” says Charla. “I always knew that I wanted to grow the team, teach them what I’ve learned, help them not stumble on things like I did, and just motivate them and mentor them to be the next great professional.” 

Charla’s leadership journey at Shipstation has taught her many important lessons.

Here are four of the learnings that stood out during our conversation:

Lesson #1: One-on-ones are your most valuable meetings as a manager

Charla finds one-on-ones the most valuable meeting out of all her regular meetings. She embraces the opportunity to learn more about her employees, share accomplishments with them, and help them get to the next level. 

Unsurprisingly, Charla’s go-to one-on-one questions include, “How can I help”, and “What can I do for you?”.  

“What I find really cool about management is when someone has that ‘aha moment’. Maybe someone has been having a little bit of a challenge, and you’ve been trying to mentor, coach them, help them. And then all of a sudden, all the dots connect.” 

Here are 3 best practices that Charla recommends to run effective one-on-one meetings: 

1 Use one-on-ones to communicate purpose to your team members

In the eyes of an independent contributor, one-on-ones can be scary and intimidating. The idea of sitting down with your manager and discussing challenges sounds daunting – like being called to the principal’s office. To overcome this perception problem, Charla reminds her team that one-on-one meetings are supposed to be mutually beneficial, and opens the floor to anything the direct report wants to chat about – whether that’s about a vacation or a specific challenge.

“I always say that that’s the time that we can talk about anything. If they want to spend time talking about going on a vacation, then we can do that. Or if they have a challenge going on, we can fully talk about that. And of course, there are some key things at different times that we just have to check through for that week or that month.”  

*If you’re struggling with what else to ask your team, here are 200 one-on-one meeting questions to get you started.

2 Add to the agenda at the beginning of the week

Charla’s weekly routine is to add talking points to her one-on-one agendas on Monday. She finds that this indirectly helps others to add their own topics and encourages her team to get involved. By using a one-on-one tool like Fellow, Charla knows that her teammates will be able to see that she has added talking points to the agenda, which might just provide the little nudge that they need to do it themselves. 

Add to that the benefit of relieving anxiety for some of your direct reports, and that seems like a pretty good practice. By creating the agenda in advance, direct reports can see what the manager would like to talk about – which removes some of the mystery around one-on-ones. 

“At the end of every one-on-one, I like to ask ‘How can I help?’, ‘What can I do?’ I think that as a manager we forget a lot that we’re also here to help them. They help us everyday, so how can we help them?”

3 Create (and reuse) a one-on-one meeting template

As a big checklist person, Charla loves her templates! Her go-to one for one-on-ones has five headers:

Here’s what that one-on-one meeting template looks like in Fellow.app

Customize your own templates in Fellow.app

Charla’s template is similar to what Monique Valcour suggests in her HBR article about how great managers are also great coaches:

“Help build connections between each person’s work and the organization’s mission and strategic objectives, provide timely feedback, and help each person learn and grow on an ongoing basis,” says Valcour. “Regular communication around development — having coaching conversations — is essential.” 

In the Feedback section, Charla has found it best to provide clear examples. For instance, if someone frequently misses deadlines then Charla would point out the times when those deadlines were missed. She also finds it useful to help discuss solutions with the individual about how they can work together to try to solve the problem. 

And as a manager of managers, Charla finds it useful to check that her direct reports are holding regular one-on-ones by using the Analytics Dashboard in Fellow. This way, she can guide them along and encourage meaningful conversations between everyone on her team. 

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Lesson #2: Help your teammates grow and develop through Career Conversations

One of Charla’s first hires was a recently graduated intern. That intern grew to become the current Partner Marketing Manager at Shipstation. Charla and this former intern have been together for three and a half years. They talk all the time about what the next level is, and how they can get there. And on a larger scale, what do you aspire to be?

For Charla, this is one of the most fulfilling aspects of her management role. She loves mentoring and engaging in career conversations. More formal conversations, where the employee can know where they stand, are scheduled each quarter. It’s a true evaluation, with pros, cons, and successes. But Charla doesn’t wait for this time each quarter. Instead, she chooses to discuss things more regularly asking, “Where do you see the next step?” and “What did you learn from that?”

In an article for Forbes, Sarah Greenberg describes coaching as the most important and desirable leadership competencies:

“If one leader overseeing a team of 30 people is attached to being the expert, while another manager leading a team of the same size excels at helping others unlock their full potential, it’s easy to imagine whose team will be most effective over the long haul.”

And after years of managing a team, Charla understands the value of investing time in her teammate’s growth.

*If you’d like to learn how to structure professional development conversations with your team, check out this blog post about Career Conversations.

Lesson #3: Promote a Growth Mindset across your team

The concept of a life-long-learner is fairly self-explanatory – someone who continues to self-initiate learning throughout their life. It’s a concept that Charla takes to heart. She does this by keeping up to date on marketing journals, publishing in companies, and educational events. As she comments, “Everything is always changing!”. 

For those who find themselves in a rapidly changing environment, Charla advises three things – adaptability, flexibility, and life-long-learning. She suggests being a sponge and soaking up as much information as you can before branching out to explore new things. 

“And being adaptable – that’s really the key because there’s been many times that I have been here when things have changed, and if I was just like ‘ahh, I can’t handle this!’ – it wouldn’t have worked out. “

However, Charla doesn’t just encourage learning and growth at the individual level. She also promotes learning and growth at a team level. Recently, Charla had her team participate in a 3-hour off-site brainstorming session. They brainstormed what they were doing well, what they could improve, along with more aspirational goals. Charla hosted different activities to help get the creative juices flowing and got her whole team to read the book, The Power of Habit

Charla and her marketing team also take part in more out-of-the-box events that help motivate the entire team. As Charla correctly points out, sometimes work can feel monotonous. So, doing something to break up the routine really helps. In October, the team went on a ghost tour followed by a visit to a boozy ice cream shop. The event was valuable for team-building and helped the members of the team to get to know their colleagues outside of the work environment. 

Lesson #4: Learn from Experience

Back in the day, there were only a few possible career paths (like becoming a teacher, a secretary, or a doctor). Nowadays, there seems to be a job for everything – leading to some pretty creative job titles. With so many options, it’s hard to decide which path to follow.

“In Marketing alone, you could specialize in brand, product, partner, digital, etc,” says Charla.

Charla recommends trying a bit of everything to see what you like and what you really don’t. Anecdotally, she shares the story of a colleague who was really focused on a career in Event Marketing. But after giving it a try, they realized that it wasn’t a good fit. They tried something else and found that they enjoyed the copy-writing aspect. 

The most important lesson here is: When a manager gets to know the person, they can help coach them in the right direction

Finally, Charla looks at past managers for what to do and what not to. For the practices that she doesn’t want to repeat, she flips them into a positive. There’s always something to learn. Conversely, Charla also likes to reflect back on the days when she was in her direct reports’ shoes, and think about what she needed at the time. 

. . .

Coaching is becoming a more and more important part of a manager’s day to day role – and Charla takes that role very seriously. 

Hopefully, Charla’s enthusiasm for mentoring and coaching can shed some light on how to help your teammates develop and become the best versions of themselves. As Valcour says, “If there’s anything an effective, resonant coaching conversation produces, it’s positive energy” and Charla certainly has that! ⚡️