Assembling a talented team is every leader’s dream. Projects move faster, company culture flourishes and new ideas come quickly.
But to keep the good times rolling, leaders have to hold onto that all-star talent. One way to do that is by ensuring individual contributors and managers have room to grow their careers.
Nurturing a team’s professional development isn’t as simple as handing out promotions and hoping for the best. Instead, leaders must invest in trainings and provide support so their team members are prepared for that next step. If done correctly, individuals can evolve into more effective leaders, which can create stronger teams overall.
To get a pulse on how executives foster growth on their teams, Built In Boston polled five local leaders to understand their best strategies for developing talent. We learned that there’s no one-size-fits-all approach — but great communication, honesty and trust are key.
What they do: CarGurus strives to make car shopping simple. Instead of roaming around a car lot all day, users can log onto CarGurus’ site and take advantage of data and smart tech tools to find their next vehicle.
Briefly describe your management style. How do you work with your direct reports?
I try to build a culture where we never take ourselves too seriously. We work hard, but I want people to enjoy it and laugh along the way. You get the best from people when they can be their true selves.
I am also extremely transparent. I firmly believe that clear is kind, unclear is unkind. I recommend the book “Radical Candor” by Kim Scott. The idea is that the optimal style of leadership is where you care personally but challenge directly. Being a leader is a huge privilege. You must care about your people. However, do not mistake caring for them for not holding them accountable. Too many leaders and new managers fall into the “ruinous empathy” quadrant, where you care but you don’t challenge.
The best advice I have for new leaders is to get comfortable with being unpopular. Never let your need to be liked stop you from being an effective leader. You will never be a great leader if you don’t learn to be comfortable with hard conversations. Also, the hardest conversations I have with my leaders are face-to-face. They know that I really care about them and go to bat for them outside of those talks.
What strategies have you found are key in empowering the managers below you and supporting them in their growth?
Firstly, I think one thing that many leaders forget is the power of vulnerability. That might sound strange, but essentially it all comes back to honesty. We are all human. I am never afraid to let my team know that sometimes I struggle. I also have to be able to apologize and admit when I am wrong. I think this invites my team to be honest with me and share their concerns, which should trickle down throughout the organization.
One thing that many leaders forget is the power of vulnerability.”
Secondly, I set very clear expectations with them so there is no ambiguity in terms of how they will be evaluated. My direct reports know that I look for excellence and set the bar high — and I expect them to do the same with their teams. Then, I leave them alone to do their jobs and come to me if they need help.
Finally, I am a huge believer in the power of sharing information. I try to always explain the bigger picture to my team, and I trust them to keep it confidential. This helps them think like owners of the business, rather than just leaders of their own teams.
What training does your company offer developing leaders to help them grow and thrive in their roles?
At CarGurus, we offer various forms of training and development programs to help our Gurus grow and thrive as leaders and people managers. Accelerate is our leadership development program, specifically aimed at new managers. The goal of Accelerate is to develop our newest people managers into capable leaders who can create the conditions for those around them to innovate, collaborate and collectively drive CarGurus forward.
The program includes a series of in-person workshops, active learning assignments, readings, videos and discussions, as well as group coaching sessions where participants build their coaching skills and deepen their learning. The program is grounded in our leadership principles, so we have a shared language for what kind of leadership we aspire toward.
What they do: SmartBear builds products that have helped more than 15 million developers create quality, reliable software. The company’s toolkit includes test automation, API lifecycle, performance testing and more.
Briefly describe your management style. How do you work with your direct reports?
I would describe my management style as a combination of coaching and teaching.
We put a great deal of emphasis on personal development and learning across our organization here at SmartBear. As with any working relationship, it takes time to understand what drives people, and then to tailor and develop different styles of engagement, management and mentoring. I’m fortunate to have a strong leadership team that I’ve worked with years. Spending time with my direct reports is big for me. We can all get lost in activities that aren’t moving the ball forward, but my direct reports do an excellent job of staying focused on big priorities.
What strategies have you found are key in empowering the managers below you and supporting them in their growth?
While it might sound obvious, taking time to listen to what our leaders have to say is the first step. They have a pulse on both our organization and the market we serve, and I’m not doing my job if I’m not listening to them. They need to be heard, and in many cases, direct action needs to be taken.
It’s equally important to allow them to take risks and to do the job they were hired for, knowing things might not always turn out as expected. If we’re hiring and promoting the right people, the odds are in our favor. We promote heavily from within, and I’m a strong believer that after a certain amount of coaching and training, the training wheels need to come off — and there is no better way to learn than in real-life scenarios.
I’m not doing my job if I’m not listening to what our leaders have to say.”
What training does your company offer developing leaders to help them grow and thrive in their roles?
We’ve seen great success in developing our individual contributor talent and providing them with the tools necessary to move into leadership roles. Throughout the year, our people team provides various trainings for our managers to help them navigate several initiatives, including goal setting, learning interview best practices, team building strategies and more.
Most of our trainings are tailored to our company’s core values, because when our managers adhere to those values it really sets them up for success. As we continue to expand, we’ll roll out additional trainings focused on the continued development of soft skills and effective communication.
What they do: Teikametrics aims to help sellers and brand owners optimize their e-commerce businesses on Amazon and Walmart.com. Using marketplace data, AI and deep expertise, Teikametrics is building tools to save sellers time, reach more customers and make more sales.
First, briefly describe your management style. How do you like to work with your direct reports?
Leadership defines the culture of an organization, so leaders need to demonstrate strong ownership, which is one of our core values at Teikametrics. Within the engineering team, I emphasize strong ownership, which helps us take on challenges. That ownership results in leaders who are not only able to do their best work, but are able to see beyond the task in their domains and find solutions to problems that arise on their own.
Once you are empowered and have the tools an owner does, you make decisions like an owner. It is critical for our entrepreneurial culture to practice this value as we scale and grow.
As a leader of leaders, what strategy have you been found to be key for empowering the managers below you and supporting them in their growth?
Talent is the only sustained competitive advantage a company has in the long run. This is what we believe across Teikametrics: our people are our greatest asset. I make decisions in support of this kind of long-term talent growth. We have to act with the strategy that we are building toward long-term success for our people and our organization.
I always lead with the focus that talent is our significant advantage.”
When it comes to helping my managers grow their team over time, I always lead with the focus that talent is our significant advantage. We have the talent and the right engineers, so everything else will fall into place. We must all work to maintain a high bar for expertise — we cannot coast. I encourage this mindset so we can continue to learn and ask questions like, “Where can we improve, learn and overcome this challenge?”
We have to keep asking, doing and learning. If we are able to maintain our own high bar for expertise, that helps others grow and support high performance.
What formal training does your company offer developing leaders to help them grow and thrive in their roles as people managers?
We have a multistep approach to give people the opportunity for growth and to move into management. We use a combination of experience-based learning, e-learning via our learning platform, manager coaching and manager training to grow from within. We focus on three areas: knowledge leads, responsibility leads and talent leads.
A tech leader’s growth begins when their manager gives them a project and empowers them to practice ownership. We encourage managers to coach to our values, like ownership, which helps them think through all the scenarios. Focusing on responsibility lets each manager run with their own solutions so they can learn what works and what fails, and how to overcome challenges along the way.
Becoming a talent lead takes a combination of mentorship and coaching. We start with one-on-one mentoring, helping them with targeted growth areas and building their strengths and successes into a career path.
What they do: Simply Business wants to make it easier for small businesses to find the perfect insurance policy. By leveraging industry partnerships with trusted carriers, the SB team works to select plans to fit individual customer needs
Briefly describe your management style. How do you work with your direct reports?
I would describe my management style as inquisitive, trusting and supportive. I enjoy getting to know my team as people and understanding what drives them as individuals. Building a strong relationship helps build amicable trust, which creates the foundation for a strong working relationship. People are better positioned for success if they understand what is expected of them and how they can contribute to the larger objective.
I keep in regular communication with my team members, like most leaders, through one-on-one conversations and team meetings, but would define my approach as more hands-off to allow them the freedom to do their jobs. I love to ask questions that drive deeper discussions and a better understanding of others’ perspectives. I find that this helps the team think through their challenges more effectively.
What strategies have you found are key in empowering the managers below you and supporting them in their growth?
I’m a big fan of learning on the job. You can talk about any challenge until time stands still, but letting leaders go out and do will always be more effective.
I first try to understand the objectives the managers are trying to achieve and how they plan to address those objectives. I provide an environment where people feel free to share their ideas and plans to better understand where I can help support them.
I’m a big fan of learning on the job.’’
I encourage my team to meet with me initially to talk through what they are thinking, even if it’s just to provide the support to move forward. “Trust but verify” is a good rule of thumb to ensure their approach and the implications are aligned to the broader objectives. Giving people that green light to go and do is very impactful — even if it doesn’t always work out.
That brings me to one of the most important aspects of empowerment. People will fail, and that’s a good thing! Creating an environment where people know it’s OK to fail, learn and adapt will create lifelong learnings.
What training does your company offer developing leaders to help them grow and thrive in their roles?
At SB, we strive to make defined leadership behaviors stick through self-reflection, coaching practice and feedback. Our Leadership Challenge program includes biweekly nudges that consist of certain challenge tasks or supporting resources. The topics vary depending on our needs at the moment. In conjunction with the nudges, we offer monthly meetups for managers to share and learn from one another. The offerings are all optional, giving our leaders autonomy and choice in what they want to invest their time and energy in.
Additionally, our leaders can engage in peer learning groups to strengthen leadership skills and build trust. We also offer more traditional one-on-one coaching via a virtual coaching platform called BetterUp. For leaders who need to focus on targeted skill development, they can work with a specialist coach.
Finally, we host company-wide leadership panel discussions, where senior leaders discuss relevant topics. We’ve found this to be a great way for our employees to connect with our leaders and for our leaders to share their personal stories.
What they do: Flywire is a vertical payments company building tools to simplify international transactions for education, healthcare and business organizations.
Briefly describe your management style. How do you work with your direct reports?
I believe in turning the organizational pyramid upside down, where I’m at the bottom and the people serving our customers (universities, health systems, businesses) and their customers (payers) are at the top. As a leadership team, our job is to set the direction and serve the rest of the organization.
For that to work, we need to understand what our employees (who we call FlyMates) need from us, make ourselves accessible, be transparent and over-communicate. We use 360-degree feedback as a foundational tool in our leadership training as one way to support that.
In addition, I emphasize the need for direct communication, empowerment and delegation. If there is conflict, we don’t want people to avoid it, but we expect them to be clear and honest. I also expect people to act on feedback. Otherwise, I take it as a sign of disinterest. Our executive user manuals provide a simple and effective way to explain to internal stakeholders what motivates you and how you prefer to communicate.
I emphasize the need for direct communication, empowerment and delegation.”
What strategies have you found are key in empowering the managers below you and supporting them in their growth?
It starts with ensuring we are all clear about our purpose as a company, and have a clearly defined culture and shared set of values. That really helps when people are making decisions — not just at the executive level, but throughout the organization.
Early on as a CEO, my mindset was that it was my job alone to keep the company moving forward and prevent it from breaking as we experienced the ebb and flow between big leaps forward and some steps backward. One big “aha!” moment for me was understanding that the company was (and is) inherently destined to break, again and again. I can’t prevent that. All I can control is getting better at identifying what is breaking and ensuring we are focused on making the changes needed to improve it. I also realized that I did not have to own it all. I need to share that responsibility with my leadership team so that they can contribute along the way.
Our focus as a leadership team is on adapting faster after things break while making sure we learn from our missteps. The better job we as a leadership team do at that, the more equipped we are to reach the next level.
What training does your company offer developing leaders to help them grow and thrive in their roles?
We are dedicated to creating a culture where our FlyMates are supported in their continued development both professionally and personally, and we invest in year-round training programs tailored to them. Our people and culture team maintains a robust learning and development program called Flywire Learns. Topics range from behavioral profiling to allyship training. Our manager training, which we call Managers Taking Flight, tackles themes such as team building, emotional intelligence, managing a high-performance remote team, managing up and more.
For 360-degree feedback, we use a tool called Situational Leadership, which provides a framework to help our leaders analyze different situations based on an employee’s readiness level to perform a specific task, function or objective. This helps leaders adjust their management behavior and communication accordingly to support employees and advance their development.
