Work with the employee to identify the performance issues or challenges they need to work on. This can be difficult to see, especially in today’s virtual and remote working environments. To learn more, ask them where they are having their biggest success, and their biggest challenges. Then find out what they feel they might need to get past that challenge. The goal is to allow them to find the answers, instead of telling them the answers or solutions.


The number one leadership initiative in any organization today is improved coaching. Coaching empowers employees, empowerment drives engagement, and engagement drives performance. At its core, coaching is about transformation. Leading distributed teams requires transforming how we coach and changing our play calls and playbooks to get things done. As a part of our interview series called “Moving From Command & Control to Coaching & Collaboration; How Leaders and Managers Can Become Better Coaches,” we had the pleasure to interview Cassandra Rosen, an international business consultant and the co-founder of FK Interactive.

Cassandra Rosen is a 15-year branding and communications expert that teaches C-suite managers and leadership teams how to create strong brands through coaching and verbal identities. Inside her agency, FK Interactive, she and her team have worked with legacy organizations like DIAGEO, Whole Foods, Marriott, and BevMo!, as well as startups and personal brands to help them scale, identify ideal customers, attract top talent, and grow market share through strong verbal brand communications. A Florida native, she currently resides in Winter Park, Florida along with her husband Kevin, and their two mini Schnauzers, Kala and Zeke.


Thank you for joining us to explore a critical inflection point in how we define leadership. Our readers would like to get to know you better. What was a defining moment that shaped who you are as a leader?

I’ve had many ‘defining moments’, but most of those came back to the fact that you can’t treat people like commodities. You have to invest in them, groom them, maintain ethics, and coach them if you want your organization to succeed.

I’ve had positive experiences with managers who gave me a shot when I had no experience, and negative ones like when I was in finance and a colleague went unpunished by leadership for a crime.

Leadership can make or break a company, and it will attract or repel good employees.

I’ve worked with clients in a lot of different businesses over the years, and what I found was that constructive leadership starts with focusing on four things: communication, cooperation, feedback and flexibility. Those core elements contributed to how we set ourselves up as a virtual agency over a decade ago, and it’s what’s help our team to thrive during difficult times.

A leader is not equal to the success of a company. In fact, their role is much greater than that. A true leader is equal to the leadership he provides to everyone else that is willing and able to contribute to the greater project at hand. It’s their collective success that is a reflection of that leader’s work and efforts.

John C. Maxwell is credited with saying, “A leader is someone who knows the way, goes the way, and shows the way.” How do you embody that quote as a leader?

For me, a true leader has to represent truth, transparency, and humility in their dealings with others. A lot of today’s leaders are anything but that, and it’s something that I work very hard at on a daily basis. It’s servant leadership.

A leader that is willing to work with their team will train them, allow employees to test the skills they’ve learned, and then provide feedback to them on what worked and what didn’t. This type of atmosphere encourages employees to flourish and creates incredibly strong brands. That’s the type of leadership I recommend, and it’s how I work with my team.

How do you define the differences between a leader as a manager and a leader as a coach?

First, it’s important to acknowledge that managing and coaching are two different activities. We can think about this like walking vs. sprinting. Both activities will take us to a destination, but the single process of how we get there is different. And not every individual can go at the same pace.

This is done is through two types of communication methods. For example, a leader communicates by influencing and motivating followers. If they are using a managing style, they’re going to be organizing and directing. That means there’s less ownership and empowerment from the employee’s perspective because the leader is calling the shots.

In contrast, if a leader uses a coaching style to communicate, they would ask an employee more questions. This stimulates participation in the conversation and the planning process, and grooms employees to think for themselves.

We started our conversation by noting that improved coaching is the number one leadership initiative in any organization today. What are some essential skills and competencies that leaders must have now to be better coaches?

The most important skill that a leader needs to master is being a successful communicator. However, that doesn’t mean just speaking. It means actively listening. The real challenge is determining which communication approach-either managing or coaching-will best fit the people and situation at hand.

The answer requires a secondary level of expertise: that of observing and analyzing skill sets and capabilities.

The situations and jobs that employees are in frequently reflect their natural abilities. A natural leader is going to be attracted to a startup, for example, because they understand organization and project management. A middle manager, however, can get stuck because leading is not natural for them. Each person needs opportunities to express themselves, to test critical thinking and relationship-building strategies, and that’s where coaching will come in. A leader that does this will help managers build resilience so that when challenging situations arise, they are prepared and better able to tolerate stress.

We’re all familiar with the adage, “You catch more flies with honey than with vinegar.” How are you inspiring — rather than mandating — leaders to invest in upskilling and reskilling?

Upskilling and reskilling are a choice. Either leaders and their organizations appreciate the value they provide, or they can do things the way they’ve always done them. The latter scenario will rarely result in positive results.

Investing in leadership coaching training has proven to build strong organizations. Statistics show that employees who are given a sense of autonomy and ownership over their work are more engaged in the process. They feel more trusted, and that trust motivates them to improve their performance.

Proper coaching also shifts the accountability from the leader to a shared responsibility with the team. This helps the team to learn, analyze situations, problem-solve, and make application when mistakes occur.

Entrusting employees also allows them to become more mindful and creates personal growth. A leader who can train and coach others to their greatest potential is more valuable to an organization than an individual who can only organize and create orders.

Leaders who learn how to coach can also create alignment with company goals, which, in turn, creates a more loyal corporate culture.

Let’s get more specific. How do you coach someone to do their best work? How can leaders coach for peak performance in our current context? What are your “Top 5 Ways That Leaders and Managers Can Be Effective Coaches?”

As a leadership coach, I would start by assessing the employee’s baseline: their current strengths and weaknesses, as well as their perception of their work. From there, we reinforce positive actions, then work with them to develop a personalized plan for improvement. This might include things like setting specific, measurable goals; identifying areas for skill development; overcoming fears; and creating a support system for feedback.

It is also important to work on building an employee’s self-awareness, emotional intelligence, and resilience, as well as creating a positive and productive work environment.

Here are five key ways that leaders can be more effective coaches, and coach employees to perform at their best level possible.

1. Establish a baseline and learn their perspective.

One of the first things we need to do when we’re coaching someone, especially on a task that’s new or perhaps out of their comfort zone, is to establish a baseline. How we do that is through asking questions and learning their perspective.

Many years ago, a client asked us to coach a family member, a young woman who had never sold anything in her life, to be their lead sales rep for a new brand they were launching. This young person was willing to learn but felt very unprepared in communicating with high-ticket buyers.

With coaching, sales scripting, and role-playing, along with a system for support, she was able to go from no sales experience to selling large contracts in less than a year’s time.

2. Find ways to give evidence-based reinforcement versus just praise.

As in sports, every coach wants to praise an athlete who’s performed well. But misplacing praise before someone has performed a task correctly can backfire. To encourage someone to continue to improve, focus on efforts instead of achievements. Then, reinforce good behaviors through acknowledgment and evidence of effort.

Back in 2018, our team was hired to coach a national sales team who had fallen very much ‘out of love’ with one of their products-a 26 SKU product portfolio. The brand had gotten into distribution, but after years of no marketing support, neither internal sales more buyers were interested in the line. Incentives had not worked. Neither had monthly sales meetings, which were intended to get staff excited and energized. Sales for the brand had nearly all but stopped.

Training hundreds of salespersons individually was impossible. The determination had to be made, where could we make the most impact? Management decided on group training for regional sales managers.

First, we polled managers to find out who, if anyone, had taken the time to read the new sales materials. A few key regional managers had made the effort to do so and were selected to represent the group as a whole. These were acknowledged for efforts made to date, and then asked a series of questions about what they liked and disliked about the new direction.

Although most concerns were no longer valid, we listened, and remained objective and confident, sharing data that supported the direction.

After approximately three months of coaching and support, total company sales started to rise. One year later, the brand was up over 145% in the US market and had more than doubled sales overseas. Their sales team was reinvigorated and were once again excited to sell the line.

3. Allow employees to collaborate on solutions.

The next step is to work with the employee to identify the performance issues or challenges they need to work on. This can be difficult to see, especially in today’s virtual and remote working environments. To learn more, ask them where they are having their biggest success, and their biggest challenges. Then find out what they feel they might need to get past that challenge. The goal is to allow them to find the answers, instead of telling them the answers or solutions.

One example of how to do that would be through the use of a short, three-question framework.

After working on a task or project, employees can learn to ask themselves:

1. Which (strategy, objective, or target) worked the best?

2. How can I verify that this is true? (what is the data or evidence)

3. Why do I know that this worked? (what data points to success)

One small business owner we worked with used this process to analyze sales data, reposition his entire marketing direction, and recapture over $300,000 a year in lost sales.

His Chief Revenue Officer also discovered which employees were losing customer leads, relocating some to other departments while others were asked to exit the company. The results transformed how and who they chose to do business with.

4. Help them to set SMART goals.

After you’ve identified what an employee needs to overcome a challenge or meet a task, it’s time to help them set SMART goals: specific, measurable, achievable, relevant, and time-based.

A good coach leans on questions to help the employee understand not just what needs to be done, but why. This also creates a more impactful long-term result, as the employee becomes more teachable, or ‘assessment capable’, a term coined by educator and author, Dr. John Hattie. This process helps the employee to check his or her own personal progress toward a goal by creating a feedback framework. This allows them to make more informed choices.

We can break this process down into three primary coaching questions that employees can learn to ask themselves:

  • Where am I going? (as it relates to the task or goals).
  • Is what I’m doing going to get me there? (how is my performance when measured against goals).
  • What steps should I take next? (related to future goals).

5. Write out an implementable action plan.

Leaders can coach employees to create an action plan by first helping them to identify their goals and objectives.

Once the goals and objectives are clear, the leader can then help the employee to break down the plan into smaller, bite-sized steps. This might involve creating a timeline or schedule, identifying resources needed, or identifying support that the employee may need to successfully implement the plan.

For example, when working with one very large national sales team, we found that there was a need to improve their presentation skills.

Buyer presentations were dated and lacked information buyers would need to make an informed purchase.

Working with key department leaders, we were able to coach them to identify what areas first need improvement; in this instance, their visual aids for the presentation.

We then worked with their team to help them write out an implementable action plan and identify resources to review competitors so that as their needs changed, they could stay up-to-date. The results were a successful presentation to the US Navy, as well as numerous travel retail buyers and sales growth.

The Ultimate Goal With Employee Coaching

The key to coaching an employee to do their best work is to work with them to understand their unique needs and motivations, and to help them develop the skills, knowledge, and mindset they need to succeed.

When we treat employees like valuable persons instead of commodities, performance goes up, commitment increases, and the organization as a whole benefits.

We’re leading and coaching in increasingly diverse organizations. And one aspect of workforce diversity on the rise is generational diversity. What advice would you offer about how to effectively coach a multi-generational workforce? And how do you activate the collective potential of a multi-generational workforce?

Business leaders can coach a multi-generational workforce by adopting a flexible approach. ‘One-size-fits-all’ will not work, so you need to be open to a variety of coaching techniques and approaches, and try new methods as needed.

Multi-generational employees need us to understand the unique characteristics, emotions, and perspectives of each generation.

For example, baby boomers may value structure and stability, while millennials may place a higher emphasis on work-life balance and flexibility. By recognizing and respecting these differences, business leaders can tailor their coaching style to better meet the needs of each employee.

To increase the potential of all employees, business leaders need to encourage a culture of learning and development within their organization. This might involve offering training and development opportunities that are relevant and applicable to employees of all ages.

Leaders can also encourage employees to take ownership of their own learning and career development. By creating a supportive environment that values continuous learning and growth, business leaders can foster a sense of engagement and create a sense of connection and belonging within a multi-generational workforce.

You’re referring to emotional intelligence, in a sense. What are two steps every leader can take to demonstrate a higher level of emotional intelligence?

There are two primary ways.

First, studies have shown that a higher level of emotional intelligence starts with being a good listener.

This means paying attention to what others are saying and seeking to understand their point of view, feelings, and needs. When leaders practice active listening, they show that they value the ideas and opinions of their employees, and are open to hearing different viewpoints.

The second way to show emotional intelligence is through empathy: making the effort to understand and share the feelings of others.

When leaders show empathy, they prove that they care about their employees and are able to connect with them on a deeper level. This can be as simple as offering a supportive word or a listening ear when an employee is facing a challenge, or acknowledging their feelings and showing understanding when they are upset or frustrated.

By demonstrating empathy, leaders can build stronger, more positive relationships with their employees, and create a more supportive and inclusive work environment.

Words matter. And we’re collectively creating a new leadership language right now. What are the most important words for leaders to use now?

That’s a good question. I would go back to the success framework I mentioned in the beginning, based on communication, cooperation, feedback, and flexibility. Here’s why.

Communication: Clear and effective communication is going to be even more crucial for building trust and understanding within a team in today’s fast-paced business environment.

Cooperation: Encouraging cooperation and teamwork helps to build a positive and collaborative work culture and keeps employees engaged.

Feedback: Leaders that provide ongoing constructive feedback help to improve performance and foster a culture of continuous learning and growth.

Flexibility: Offering flexibility in terms of work arrangements and schedules can help leaders to support the diverse needs of a multi-generational workforce. Not everyone wants or needs a 40-hour-a-week job, and offering options will help you attract the best talent.

I keep inspiring quotes on my desk. What’s your favorite “Life Lesson Quote,” and why does it mean so much to you?

One of my favorite life lesson quotes is from Theodore Roosevelt. He said, “The best leader is the one who has sense enough to pick good men to do what he wants done, and the self-restraint to keep from meddling with them while they do it.”

When you choose the right people, give them the right tools and then get out of their way, you’re allowing them to take ownership. And ownership creates a level of value and commitment that you can’t get from only managing.

It’s our responsibility as leaders to inspire others and help them to manifest their fullest potential. If we can inspire our team, collaborate on a plan, and then allow them to feel so empowered, they think they did it all themselves, then we’ve done our job well. And that’s how strong organizations can continue to thrive and grow.

Our readers often like to continue the conversation. What’s the best way for readers to connect with you and to stay current on what you’re discovering?

Anyone who knows me knows I’m a big fan of LinkedIn. I’m a firm believer that network is one of the most powerful places for leaders to be seen and heard, especially if they want to become authorities in their space.

If readers want to keep in touch, I’m happy to connect with them on LinkedIn.

I’m also available directly through our business leadership consulting agency, FK Interactive, or they can email me through [email protected] and our team will get those messages to me.

Thank you for a meaningful conversation. We wish you continued success with your mission.