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How Do Leaders Cultivate Leadership Skills Within their Teams?

How Do Leaders Cultivate Leadership Skills Within their Teams?

In the pursuit of excellence, executive leaders often play a pivotal role in nurturing the next wave of leadership within their organizations. From implementing a mentorship program to embracing servant leadership, we've gathered perspectives from eighteen CEOs, Founders, and Executive Directors. These seasoned professionals share their firsthand experiences on effectively cultivating leadership skills in their teams.

  • Implemented a Mentorship Program
  • Provided Growth Opportunities
  • Encouraged Mentorship and Challenges
  • Addressed Personal Biases
  • Empowered Team During Pandemic
  • Focused on Appraisals and Real-Time Learning
  • Practiced Restraint in Feedback
  • Aligned Work with Human Needs
  • Hosted Teach-and-Learn Meetings
  • Recognized and Leveraged Team Strengths
  • Aligned Roles with Skills and Aspirations
  • Launched a Leadership Development Program
  • Fostered Curiosity and Problem-Solving
  • Empowered Team in 'Phoenix' Project
  • Adopted 'Lead by Doing' Approach
  • Implemented 'Mini-CEO' Concept
  • Guided Team to Self-Discovery
  • Embraced Servant Leadership

Implemented a Mentorship Program

One impactful example from my experience involved implementing a mentorship program within our leadership team. We paired seasoned executives with emerging leaders based on complementary strengths and growth areas. Through structured monthly sessions, mentors guided strategic decision-making, stakeholder management, and personal leadership development. This program enhanced leadership capabilities across the board and fostered a culture of continuous learning and collaboration. Seeing mentees grow into confident leaders who, in turn, mentored others, reinforced the program's success. It exemplified how investing in mentorship can cultivate a robust leadership pipeline and strengthen organizational resilience.

Josh Burris
Josh BurrisCEO, STNDRD

Provided Growth Opportunities

As CEO of Genius Solutions for over 27 years, I have focused on providing growth opportunities for my team to develop leadership skills. For example, when an accounting clerk showed interest in project management, I had them lead the implementation of a new timekeeping system. Giving them full control of the project allowed them to gain valuable experience leading a cross-functional team through a complex process. Upon completing the project, their new leadership abilities have benefited the entire organization.

We also rotate team members between departments to expose them to new challenges and build understanding across roles. Recently, an engineer spent 6 months working with our services team to strengthen their technical knowledge. When they returned to engineering, their experience providing customer support allowed them to lead the redesign of our help resources, which improved the customer experience.

During annual reviews, I ask each team member about their leadership and career goals. If someone aims to improve presentation skills, I have them lead a session in our internal education program. When a business analyst wanted to better understand industry regulations, I tasked them with briefing our executives on new compliance standards. Tailoring growth around individual aspirations keeps my team engaged and develops the leaders that will shape our future.

Jean Magny
Jean MagnyPresident, Genius Solutions

Encouraged Mentorship and Challenges

As an entrepreneur without a degree, I've had to develop leadership skills through experience. Early on, I struggled with feeling like an imposter, managing people far more educated than me. I overcame this by focusing on my fresh, practical knowledge and by taking online courses to strengthen my foundation.

For example, when acquiring a new company, I had to integrate their team into our culture. I spent time with each employee, learned their roles and concerns, and involved them in key decisions. By demonstrating interest in their work and career growth, they gained confidence in my leadership despite my lack of credentials.

I also encourage leadership development through mentorship and by providing challenging opportunities. For instance, when expanding into new services, I asked a project manager to lead the launch. She gained valuable experience, now benefiting our company and clients. Through understanding various responsibilities, our team can step up when needed and suggest improvements.

Cross-training and open communication are key. Meetings discuss customer feedback, changing priorities, and training, keeping the team engaged and able to evolve with our business. Clients see the results in our expertise and ability to collaborate.

Will Mitchell
Will MitchellFounder, StartupBros

Addressed Personal Biases

Fostering strong leadership within a team means setting aside your own personal ego. As CEO of a recruiting firm, I've more than once had to dig deep and ask myself if I'm vetoing an idea because it's simply too good. Consciously, this is a decision I would never make, but I understand that biases operate subconsciously, and occasionally I've had a worker so impressive I think on some level my own identity felt threatened.

Reducing my pride took meditation and reframing. I made regular efforts to see my agency as a collective and moved away from the idea of singular ownership. Reading books about successful teamwork helped, as did embracing Zen practices. Buddhism has a lot to say about letting go of one's self!

So, if you feel your team isn't cultivating leadership within, look to yourself. It's possible you're sabotaging their efforts in some way without meaning to, through inadvertent negative talk or a stifling attitude borne of your own self-importance.

Rob Reeves
Rob ReevesCEO and President, Redfish Technology

Empowered Team During Pandemic

Leadership involves dealing with challenges, being adaptable to change, and finding solutions, among other things. One example of how we've cultivated leadership at Science Club for Girls in our team occurred during the pandemic when there were obstacles everywhere. We asked each member of the team to examine and question how we'd done everything in the past, and since most of our conventional approaches were then unavailable to us, gave them license and agency to propose and implement solutions.

The result was that the team came up with new programs and methods born from a tremendous amount of creativity and innovation, which resonated so resoundingly well with our various stakeholders that we are continuing almost all of them into the future. Building trust, communication, and support within the team was key to making these efforts successful. All of this combined to give our team a great deal of confidence in their ability to address challenges and to listen and respond to the needs of our communities, which in turn made them stronger leaders.

Bonnie Bertolaet
Bonnie BertolaetExecutive Director, Science Club for Girls

Focused on Appraisals and Real-Time Learning

I am a staunch advocate for growth within my team and myself. Within my team, appraisals are crucial, not just for evaluation but for identifying and tracking new skill sets that may need fine-tuning to unlock opportunities for success.

Leadership, in my view, is a conscious effort to support my team's individual and collective growth through target setting and performance appraisals. As a team, we set targets, and while I actively work to close my own transactions as the lead, I also create an environment for firsthand experience and modeling. From closing deals to building networks, I ensure they are exposed to communities that encourage them to aspire for leadership and meet the expectations of higher roles. This hands-on approach allows them to observe effective strategies in real-time, access clientele that increases their confidence to deliver, and meet the expectations of the firm.

I believe leaders should create opportunities for all levels of management to excel by providing them with platforms to demonstrate their capabilities. At our organization, we build a structure where each role includes executive functions similar to the level above, creating a practical training ground. This allows for error margins, correction, and real-time development.

I've learned that marrying technical competence with operational etiquette is invaluable in business. This approach ensures our employees are not only skilled but also adept in professional behavior, fostering successful business dealings. Leadership, in my view, is a job that requires both training and opportunity to thrive.

Achieving optimal performance in lean teams requires a delicate balance, a dynamic that is nuanced in certain sectors in Nigeria. Central to success is building a culture of support and inclusion, which cultivates commitment and motivation and instills a sense of ownership among team members. Building loyalty and dedication emerges as crucial drivers, empowering teams to deliver excellence consistently and enabling leaders to effectively steer towards shared goals.

Niyi Adenubi
Niyi AdenubiExecutive Director, Commercial, VFD Group Plc

Practiced Restraint in Feedback

One thing that I practice is biting my tongue! I learned as a parent that if I'm always giving 'feedback' or questioning the decisions of others, it undermines their sense of independence and confidence. There are times when I need to be okay with my staff doing things their way, even if it's not the way that I would do it. I find this challenging, but it has resulted in some great outcomes for the staff person and even the organization.

Rhonda SmithExecutive Director, Haiti H2O: Hope to Opportunity

Aligned Work with Human Needs

I work with team members to help them understand their six human needs—certainty, variety, significance, connection, growth, and contribution—and how these needs relate to performance, happiness, growth, and fulfillment at work. My wish is that they will honestly assess whether they are having these needs fulfilled in their position, and if not, what can we do to change that. As employment tends to be, certainty can be the most difficult to achieve, but that doesn't mean we cannot foster a sense of psychological safety in a team. We once had a team member who didn't want to serve on committees. I explained that you never know who you might serve with, and that those people could be a source of connection as they move forward in the company. Any achievements the committee made would grant them a sense of contribution. It's not first about team output, but rather seeking a sense of purpose, of fulfillment at work. Results always follow, and while achieving those results, you're helping people grow professionally.

Chris Reimer
Chris ReimerDirector of Marketing and Communications, Arch Grants

Hosted Teach-and-Learn Meetings

As a small nonprofit, we cultivate leadership within our small team by holding Teach-and-Learn meetings once a month. These meetings are led by a team member who teaches the rest of our small team something about the impact of their position within the organization, unique life skills, or a combination of both. The agenda is left for the team member to design however she'd like to showcase her specific leadership style, and creates a culture of constant teaching and learning within the staff, as well as cultivating leadership skills of staff who are not necessarily in leadership positions.

Amy Bickleman
Amy BicklemanExecutive Director, Global Resource for Advancing Cancer Education

Recognized and Leveraged Team Strengths

Supporting leadership development among my team means recognizing each individual's strengths and areas of opportunity, while also understanding the greater role the team member plays on the team. This helps to ensure that they are each learning from one another, in addition to coaching and learning opportunities that come up within each department. Leveraging the team's collective strengths also helps me gain insights into what bigger challenges our team is facing. With this understanding, I am able to host trainings and development opportunities that help to build the skill sets needed to run our operation successfully.

Leadership skills are built upon every day in our organization through problem-solving and collaboration, but also intentionally through acknowledgment, vulnerability, and introspection.

Preet KaurExecutive Director

Aligned Roles with Skills and Aspirations

I cultivate leadership skills by identifying the strengths and interests of each team member, allowing me to assign roles that align with their skills and career aspirations. As a leader, I also mentor team members through regular one-on-one meetings, providing guidance and support to help them achieve their goals. Encouraging open communication and collaboration, I facilitate regular team meetings where everyone can share their progress, challenges, and ideas. To inspire excellence, I acknowledge and celebrate both individual and team accomplishments. By creating an environment that fosters empowerment, mentorship, initiative, collaboration, and recognition, I help team members develop their leadership skills and contribute more effectively to the project's success.

KENYA HAYWOODEXECUTIVE DIRECTOR, CARES Inc.

Launched a Leadership Development Program

Mango Innovation recognizes team members who demonstrate leadership potential, regardless of their current position. The chosen individuals participate in a three-month program where they work on real-world projects essential to the company's success. This initiative includes mentorship, skills development, and peer collaboration as its core components.

Mentorship is facilitated by pairing each participant with a member of our senior leadership team. These mentors provide guidance, share their experiences, and help navigate the challenges that arise during the projects. This one-on-one interaction not only enhances leadership skills but also strengthens connections across different levels of our organization.

Skills development is a critical aspect. We conduct workshops that concentrate on leadership skills such as strategic thinking, effective communication, and decision-making under pressure. These workshops are facilitated by both external experts and internal leaders, offering diverse perspectives and insights.

Peer collaboration is encouraged through group projects. Participants are divided into small teams to work on initiatives that require cross-functional collaboration. This setup helps them understand the intricacies of leading a diverse team, emphasizing the importance of teamwork and collective problem-solving.

At Mango Innovation, we have seen significant growth in the roles of our participants. For example, one of our developers who completed the program last year successfully transitioned to a project manager role. He now leads a team of ten. His journey from being an individual contributor to a team leader demonstrates the tangible impact of our leadership development efforts.

By investing in our employees in this manner, we not only improve their skills but also cultivate a culture of ongoing enhancement and leadership at all levels of our company.

Derrick Boddie
Derrick BoddieSenior Web Developer & Executive Director, Mango Innovation

Fostered Curiosity and Problem-Solving

We practice curiosity. When a team member comes to me with an issue, I'll ask a series of questions to help them work through it. Doing this together helps them develop critical-thinking skills. Their problem-solving ability is enhanced, which improves their decision-making skills. These skills are necessary as they grow within our organization to eventually lead teams themselves.

Kim Wilkisson
Kim WilkissonExecutive Director, New Jersey Angels

Empowered Team in 'Phoenix' Project

One memorable instance of nurturing leadership skills within my team happened during a project we affectionately called 'The Phoenix'—a seemingly impossible rebuild of a client's crashed site with a tight deadline. Instead of micromanaging, I gave team members ownership over various components, empowering them to make decisions and even assign mini-tasks to their peers. Watching them step up, troubleshoot, and support one another was like seeing a group of apprentices forge their own swords. It wasn’t just a test of their technical skills; it was a crucible for leadership. By the end of the project, not only did we have a triumphantly resurrected website, but I also had a team brimming with newfound confidence and camaraderie, ready to tackle whatever challenges the digital world could throw at us.

Patrick Deja
Patrick DejaCEO & Founder, Codi.pro

Adopted 'Lead by Doing' Approach

One of the most effective ways is by implementing a "lead by doing" approach. Early on at Sartoro, I identified a team member with potential but lacking confidence. Tasking them with leading a small project, I provided guidance but allowed them the autonomy to make decisions. Watching them navigate challenges and come up with creative solutions not only boosted their confidence but also showed the rest of the team that leadership isn’t about a title but about initiative and problem-solving. This approach developed their leadership skills and fostered a culture where everyone felt empowered to step up. Plus, seeing them succeed was like watching a plot twist in a great movie – unexpectedly satisfying.

Andrew Fine
Andrew FineFounder, Sartoro

Implemented 'Mini-CEO' Concept

I've cultivated leadership skills within my team by implementing a "mini-CEO" concept. This approach involves giving team members full ownership of specific projects or initiatives, allowing them to make decisions, allocate resources, and drive the project as if it were their own business. This method encourages accountability, innovation, and confidence, as team members learn to navigate challenges and lead their initiatives to success. By treating these projects as their own, they develop critical leadership skills in a real-world context, preparing them for more significant responsibilities in the future.

Dinesh Agarwal
Dinesh AgarwalFounder, CEO, RecurPost

Guided Team to Self-Discovery

As a leader, we can often default to our own expertise. When someone comes to us with a problem, it's faster and easier to just give an answer with a solution. However, this does not develop leaders within our organization. Instead, I have had to learn to slow down and ask thoughtful questions back. In this way, I act more as a guide to allow the person to discover the answer on their own. For example, someone has a client issue and is asking, 'How should I handle this situation?' Rather than rattle off an answer, I will ask, 'If you were the client, how would you want the situation handled?' or 'How do you think I (or someone they admire) would handle this situation?' or 'What are your options right now?' This empowers the person to step into their leadership and make critical decisions on their own, ultimately developing independent leaders within our organization.

Tara Geraghty
Tara GeraghtyFounder, Hey Girl You Can

Embraced Servant Leadership

At Protect Line, we believe in servant leadership, which means working with each team member individually to build their core skills. Instead of a one-size-fits-all program, we take the time to understand each person's unique strengths and aspirations. This way, we create personalized development plans that empower everyone to bring their best selves to work.

This approach has created a culture where everyone feels valued and supported. Leadership here isn't about seeking individual glory but about lifting others up and growing together as a team.

Chris Reed
Chris ReedExecutive Director of Marketing, Protect Line

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