Leaders are not born; they’re made.
Many have heard the phrase “natural-born leader.” The concept of a natural leader, however, is at odds with the learned qualities and skills that collectively define successful leadership.
At five Chicago companies that promote from within, the journey from individual contributor to people manager is marked by teachable moments, mindset adjustments and self-reflection. Adapting to a leadership role presents unique challenges and new demands, and these managers offer an invaluable glimpse into how they’ve honed their skills.
For CardX’s Manager of Client Operations Alexa Krout, the ability to acknowledge unknowns is vital to managing well. “Don’t be afraid to ask questions and ask for help. There’s strength in knowing when you need to phone a friend and pull on others’ strengths.”
Meanwhile, Grubhub’s Manager of Corporate Sales Michelle Morales explained why leaders must be mindful of what makes team members’ tick. “I’ve found that in order to be a successful manager, your goal should be to figure out what motivates each person on your team and to harness that to drive their individual success, which ladders up to the overall team’s success,” she said.
These managers and three others described their journeys to management, the challenges they overcame during their transitions and the advice they have for aspiring leaders.
Grubhub is a global food delivery marketplace used by over 33 million people.
Describe your growth journey from individual contributor to manager. How did your company, team or manager help you grow into this position? What resources did you use to develop the necessary skills?
When I got hired as an enterprise sales rep at Grubhub, you were either an enterprise sales rep or a manager — there was no set career path in between. Working with leadership and the sales team, we created a senior ESR role to build a path between being a rep and a manager, and I became one of the pioneers to go through this path. From there, leadership and I agreed that a national sales role was the next step, and I was tasked with closing $1 million-plus deals with Fortune 1,000 companies nationwide. Over the years, the sales team got more resources to help with prospecting and reporting, including LinkedIn Sales Navigator, SalesIntel and Salesloft, which aided in my own development toward fulfilling a managerial role. From there, I moved to a management role, given my experience selling every type of deal — both in use case and deal size. At this point, I was ready to take all of that knowledge I had learned as a sales rep and lead and mentor a team of people like me.
What is the biggest challenge of transitioning into management, and how are you overcoming that challenge?
The biggest challenge is the loss of control of having my own book of business to close. Instead of relying on my own sales skills to succeed, my success is now determined by my ability to hire and mentor high-performing sales reps, and every single person operates differently. I’ve found that in order to be a successful manager, your goal should be to figure out what motivates each person on your team and to harness that to drive their individual success, which ladders up to the overall team’s success.
I’ve found that in order to be a successful manager, your goal should be to figure out what motivates each person on your team and to harness that to drive their individual success.”
What advice do you have for individual contributors who have recently been promoted to a management role or hope to be in the future?
Spend the time to learn your business as an individual contributor before moving over to management. This will garner you respect off the bat and will decrease the learning curve. Shift your mindset from “I” to “we.” You are now part of a collective effort, and it’s important to make your team members feel valued, appreciated and understood. Individual contributors will work harder for a leader they truly like as a person, so treat others how you would want to be treated in their position. Most importantly, keep in the forefront of your mind that your success is dependent on their success, so work together as a unit and lead by example.
Machinio is a marketplace for buying and selling machinery and equipment.
Describe your growth journey from individual contributor to manager.
I started as an account manager and became a team lead one and a half years later. At first, I was a bit wary of the transition, but it could not have been any smoother! My manager has been the best mentor, and I learn so much from his experience and interpersonal skills. I got the chance to mentor new colleagues to practice my leadership skills before becoming a team lead.
As we were growing the team, I became a team lead. We hired and trained three new colleagues. It is a very rewarding process to build up your own team! My manager and co-team lead have been invaluable resources and support; I can always discuss tricky cases with them. We are a great team and can contribute different skills and mentalities.
What is the biggest challenge of transitioning into management, and how are you overcoming that challenge?
Before, I could focus on my portfolio and do my thing fairly independently. Suddenly, I had many more meetings and trainings, and I had to transfer the majority of my client portfolio. As team lead, I need to think more about other people’s needs and struggles. We all work in different styles, and that is OK.
I needed to find the right balance of independence and oversight. After many trainings, they eventually need to walk independently, and you need to let them make mistakes so they can learn. Sometimes you need to have tough conversations, but I try to make sure they feel seen by celebrating their small and big wins with them.
Sometimes you need to have tough conversations, but I try to make sure they feel seen by celebrating their small and big wins with them.”
What advice do you have for individual contributors who have recently been promoted to a management role or hope to be in the future?
Communication! Ask questions and listen. How would your team members like to move forward? Try to get to know them on a personal level. What is happening outside of work? What’s on their mind? What motivates them? How can this be a nurturing environment in the long term? Listen to them and make sure they feel seen and valued.
Medtelligent’s flagship product ALIS — Assisted Living Intelligent Solutions — is used by assisted living companies.
Describe your growth journey from individual contributor to manager.
I started with Medtelligent in October 2021 as a customer support rep and quickly realized how much I enjoyed working for this organization and in the assisted living field. Utilizing support skills that I had developed in previous jobs, approaching the ALIS software with a desire to learn and focusing on Medtelligent’s value-based approach, I was presented with the opportunity to move into a support team lead role.
My managers and really the entire organization have spent a lot of time and energy making sure that I am supported and expectations of the new role are clear while providing leadership training to help set me in the right direction. Each step of the way, I have been able to check with my managers, go over what has been working, what hasn’t and how I can approach the role and specific situations differently. I would say the most meaningful resource that Medtelligent provides in all roles is trust and time. One of our core values is “assuming good intentions,” and people truly practice that here. When problems arise, they are always approached as a teachable moment and an opportunity to get better. Everyone is also so ready to spend time helping, which helps immensely.
What is the biggest challenge of transitioning into management, and how are you overcoming that challenge?
Stepping into a management role is uncomfortable in all the best ways! All of the day-to-day tasks that a person succeeds at and is comfortable with that typically lead them to become a manager are no longer your responsibility. Instead, your responsibility becomes making sure that your team as a whole is operating at a high level. It really comes down to a mindset change and increasing your level of awareness.
Something that one of my managers really helped me with is the pace at which I approach problems. As an individual contributor, you are often taught that speed and repetition are crucial skills to have. As a manager, the approach shifts. It is less so about getting something done quickly and much more about slowing down and looking at all of the pieces of the problem. Maybe you need additional training to solve a problem, or maybe the process is outdated and needs to be updated. Regardless of what the problem is, I am trying to slow my process down and look at all of the pieces that go into the problem and diagnose what the larger issue is as opposed to just resolving the one-off issue.
As a manager, it is less so about getting something done quickly and much more about slowing down and looking at all of the pieces of the problem.”
What advice do you have for individual contributors who have recently been promoted to a management role or hope to be in the future?
My biggest pieces of advice for anyone in management or looking to go there are to be open and accepting of failure and to lead with compassion. I have tried different ways of communicating with my team that just did not work. At first, it was hard to accept that, but without accepting it, I was continually making the same mistakes over time. Once I started to learn to reflect on something I said, how it was said, how it was received and if I achieved what I was trying to accomplish, I was quickly able to start determining what was working and what wasn’t working. Be open to those honest conversations with yourself and lean on your managers to help you sort through what went wrong and what can be done better.
Secondarily, approach all situations with compassion. Medtelligent does such a phenomenal job of this, so it has been very easy to continue that trend, but approaching any scenario that being a manager may present with compassion levels the field for everyone. Compassion deescalates possibly sensitive conversations and issues while still allowing for clear communication on what the group is trying to achieve.
CardX provides solutions that allow businesses to accept credit cards at no cost.
Describe your growth journey from individual contributor to manager.
Since starting my career, I knew I wanted to be in a leadership role. I’ve always loved working with people and helping others succeed. From the start, I shared my goals of being a people leader with my managers, and we were able to work together to create a growth plan that worked well for everyone. My growth into management came pretty naturally as a result of having these early conversations as well as being the most tenured member of the team.
I’ve read many books and articles about what good leadership looks like and how to implement these practices in my day-to-day work. I also try to use my real-life interactions as learning experiences. When my manager does something that I like or even something I don’t like, I try to replicate or change and implement it into my everyday practice.
What is the biggest challenge of transitioning into management, and how are you overcoming that challenge?
The biggest challenge of transitioning into management has been finding time to focus! I try to always be available for my team to answer questions, work through a difficult ticket together, or take an escalation call, which can make it difficult for me to focus for prolonged periods of time to complete items on my to-do list.
I overcame this by staying organized with a detailed to-do list. I keep a to-do list of all tasks and prioritize accordingly due to urgency and deadlines. I take the first 30 minutes of my day to catch up on what’s going on in our shared queue and help get everything cleaned up to help set ourselves up for success that day. From there, I will take a look at my to-do list, see if there is anything I can check off and make a game plan on the items I’m going to prioritize completing that day. I’m also big on blocking out designated time on my calendar to focus on completing work but also remain flexible, knowing anything can happen to prevent me from using that time.
What advice do you have for individual contributors who have recently been promoted to a management role or hope to be in the future?
Lead by example — you can’t expect your team to do something if you’re not willing and able to do it yourself. Don’t be afraid to ask questions and ask for help. There’s strength in knowing when you need to phone a friend and pull on others’ strengths. This means it’s important to know your own strengths and the strengths of those around you so you can work together and succeed.
Lead by example — you can’t expect your team to do something if you’re not willing and able to do it yourself.”
Lastly, give yourself grace. It’s not always going to be easy, and no one will look down on you for admitting you don’t know or need help. And on the flip side of that — be understanding and empathetic of what others may be going through.
Gearset is a DevOps release management tool for Salesforce.
Describe your growth journey from individual contributor to manager.
I’m a big believer that you don’t get anything you don’t ask for. I let my team, manager, and other executives know that I wanted to lead the team.
First, my team — or co-workers at the time — wanted someone with a background in the position and, ultimately, their respect. I focused on being a team contributor just as much as an individual contributor. This made the move to management natural for the team and me.
I focused on being a team contributor just as much as an individual contributor. This made the move to management natural for the team and me.”
Secondly, I would bring up the idea and what I was doing to my manager in every one-on-one meeting. My manager started asking for my input on strategy, and they’d assign me tasks to help identify and strengthen the key skills for management. This provided a clear picture of what I’d give to the team as a leader. As a manager, you’re adding value to the team that reports to you, but you also want to show the company you’ll add value to them by leading.
Lastly, I would bring it up to other executives. Just because a group may not be impacted by your current day-to-day work doesn’t mean they won’t have a say in you becoming a manager. This group can be powerful champions at the table when the discussion of your career and move to management is brought up.
What is the biggest challenge of transitioning into management, and how are you overcoming that challenge?
Accepting that I don’t have to be the best at everything or lead every project. I was worried that my team would lose respect for me if I didn’t know the answer to everything and was more hands-off on projects. I’ve found that they want to own certain knowledge domains and get the chance to lead projects that interest them. I have one team member owning a major product development project that could change our product drastically. I have another team member owning the training of a new hire. Both are doing an excellent job while enjoying their day-to-day work more.
What advice do you have for individual contributors who have recently been promoted to a management role or hope to be in the future?
Don’t lose passion for your industry and the role you were doing as an individual contributor. If you’re taking a management role because you don’t want to do the work of an individual contributor anymore, then management is probably not for you. Your team will quickly pick up that you feel this way. This will lead to them not seeing value in you leading them.
We’re trained to say, “the customer always comes first.” This is absolutely true to the business but, as a manager, I’d argue that “your team always comes first.” If you work with each individual to help them align with their career goals and build their brand, they’ll see value in you leading them and stay at the organization for a long time.
