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Part of being a great manager is knowing when to use certain approaches to leading. While coaching isn’t new, in the last 25 years coaching in the workplace has become more widely accepted. It’s important not to overcomplicate what coaching is and to recognize what it isn’t (it’s not therapy or feel-good fluff).

In its simplest definition, coaching is facilitating positive change with individuals and teams to unlock potential. This happens through a subtle nuance in how the leader communicates and empowers the team member to own their experiences.  Effective coaching is also learning by…coaching. You can’t learn to coach by just reading a book or taking an online course. It’s a leadership skill that is honed over time.

Coaching Skills: It all starts with Listening

Active listening is one of the most critical fundamental leadership coaching skills you can develop. When we are actively listening we are NOT interrupting, interjecting our own stories and thoughts. We are OTHERS focused. We might ask some clarifying questions and comment on what the person is saying:

  • It seems like you are really frustrated with the current situation, is that fair to say?
  • Can you say more about __________ (Insert something you aren’t clear about)
  • You’ve shared this challenge with me a few times, are you noticing any pattern?
  • I want to thank you for coming to me with your feedback about the project. I really appreciate your attention to detail. 

As you listen more intently, your team member will share information with you that can help clue you into asking the right questions. The coaching approach here is to keep the focus off of yourself, your knowledge, and your ideas. Yes, it’s true. Coaching is not about you.

Coaching Skills: Asking & Goal Setting

Once we are empowering team members in doing their own thinking, it’s important to support team members in making their ideas actionable. The next two critical coaching skills for managers to explore are powerful questioning and goal setting.

Powerful Questions 

Part of learning this coaching style is ASKING before launching into TELLING. Many people believe that they are great coaches, but they are often great MENTORS, sharing expertise. Here are a few examples of powerful questions effective leaders use:

  • What is the next step here given the goal you’ve set for yourself?
  • What would it look like if this problem were solved?
  • What would be the impact on you if you received this promotion?

Goal Setting

Ideas die unless they become actions. A good coach helps team members transform ideas into action.

  • What is a goal you could set to help avoid this problem in the future?
  • How can I support you in your goal to be promoted to leadership?
  • What best practices would you need to adopt to support you in accomplishing your goal?

When To Use Coaching…and When Not To Use Coaching

That might all sound great, but am I constantly questioning everyone on my team? The answer is: NO. If someone asks you where a file is located, you are not going to respond: Well what would be the impact on you if I found that file?

You are going to give them the file or direct them on how to get it.

Part of understanding when coaching employees in the workplace is to understand more about its intent: to develop the competence and confidence within individuals by inviting them to do their best thinking. Here’s when you want to use coaching:

  1. When an employee is repeatedly coming to you with the same issue. 
  2. When a team member is having interpersonal issues with another team member. 
  3. When a team member expressed a desire to move up within the organization.
  4. When preparing a team member to take on new responsibilities.

As you continue in your leadership role you’ll develop the intuition and emotional intelligence to know when to coach and when not to coach.

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The GROW Model For Coaching

The GROW coaching model, designed by Sir John Whitmore is one of the easiest to execute applications of coaching in the workplace. Follow these simple steps in a formal or informal coaching conversation for optimal results. With each step of the model, you’ll find helpful questions to guide you at the facilitator.

Goal: The coaching process starts with establishing a goal. It could involve performance goals, development goals, problem-solving, decision-making, or a goal for the coaching session. 

  • What do you want to achieve from this conversation?
  • What do you really want?
  • What would you like to accomplish?
  • What result are you trying to achieve?
  • What outcome would be ideal?
  • What do you want to change?
  • What would the benefits be if you achieved this goal?

Reality: Next you want to get a read on the current state or situation.  What is actually happening or NOT happening? Great managers take it slow here and leverage their active listening skills:

  • What is happening right now in a nutshell?
  • What steps have you already taken to reach your goal?
  • On a scale of 1 to 10, how confident are you that you can accomplish this goal/resolve this problem?
  • What strategies have you used in the past that were successful?
  • What is the single biggest obstacle standing in the way of you achieving your goal?
  • What is working well right now?
  • What could you do better this time?
  • What could be another possible interpretation of what _________said or did?

Options: Once you both have a clear understanding of the situation, the desired goal, or the problem, the coaching conversation turns to what the team member can do to reach their goal. 

  • What are your current options?
  • What is the best next step you could take here?
  • What would happen if you did nothing?
  • What has worked for you already? How could you do more of that?
  • What is the most challenging part of this particular goal?
  • What is a similar situation you’ve faced in the past and what did you do to resolve it?
  • What has helped you achieve goals in the past?
  • What’s the upside/downside of your options right now?
  • What option is your gut telling you to try first?
  • How would you like things to go if there were absolutely no limits?

Will or Way Forward: You close out a coaching conversation by gaining commitment from your team member on specific actions they are going to take on. This is where the person begins to own their results. 

  • What do you think you need to do right now?
  • What does success look like here?
  • How can I support you with your desired result?
  • Is there anything missing from your plan or next steps?
  • What will one small step you take now?
  • Is there anyone else you need to have a conversation with to ensure your success?
  • Do you need to block time on your calendar for any relevant actions?
  • When should we check back in on your progress?

It may seem like a lot of questions, and the truth is a successful coaching conversation is one where you don’t say much. You teach others to lead themselves. At times team members may get frustrated and just want to be told what to do. This is the path of least resistance for some, but in the long run, it keeps them stuck. 

And in the midst of it all, remember that there are times when a leader needs to step in and be very direct in their approach in order to add clarity to a situation. This isn’t a coaching skill, but is a valuable tool that you’ll still need as you lead.

We hope this list of effective coaching skills for managers has helped you. To learn more about how to develop coaching skills, download our e-book right now for free.

About Stephanie Licata

With more than two decades of leadership and management experience, Stephanie Licata is a skilled professional coach, adult learning specialist, consultant and speaker. She has trained thousands of leaders and managers in the art and science of coaching as part of large-scale projects to develop coaching cultures within organizations. Stephanie received her professional coaching certification from New York University, and is also certified at the ACC level with the International Coaching Federation. She holds a BS in counseling and a Masters in Organizational Psychology from Columbia University.

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Finding satisfaction in your career has become harder with the changing work landscape and a constant buzz of social media notifications. Companies are moving towards initiatives that include new and foreign hour structures, virtual meeting styles, digital workspaces, and more. For many, developing these new skills can be overwhelming.

Job coaching has come a long way from the days of fluorescent-lit rooms with slide screen presentations. Now, with new technologies and modern connectivity at our fingertips, learners have an opportunity to step out of those well-lit rooms and into a sunnier digital space of personalized, quality-driven, job coaching.


What is Job Coaching?

Job coaching comes in many forms and plays an important role in creating interconnected teams, improving employee communication and interpersonal skills, increasing work awareness, and understanding others’ needs alongside one’s own. From executive officers to new hires, there is a spot for everyone but not everyone has taken advantage of these new opportunities. Let’s go over some differences in coaching styles and see some ups and downs.

What is Executive Coaching?

Executive coaching or executive development is an agglomerate phrase and a well-known term covering several mentoring subcultures. From one-on-one mentoring to executive seminars, these coaching styles focus on educating the top of a traditional org chart to better position the business for success or help the CEO make better decisions. In a sense, it’s traditional coaching but there can be a variety of variations that tailor to the needs of the individual.

Despite the high profile, Executive coaching has ups and downs. It is a nebulous term that often encompasses wide-spanning terminology such as goal setting, personal development, and individual success. These terms are notoriously vague and many can see no improvement due to murky goal setting. Despite the terminology, Executive Coaching often leads to a highly focused coaching style that caters to the individual benefits of business leaders but at an often high price per session.

What is Coaching On Demand? 

Coaching on demand is a version of executive coaching that is targeted to early and mid-career professionals. This type of coaching is typically booked online through an app or website. Most sessions are virtual, facilitated by a certified coach, and are offered at a steep discount compared to other types of executive coaching. 

On-Demand coaching like this makes executive level coaching accessible to more people. A professional schedules an appointment at a time convenient for their schedule or for a specific challenge, and the two parties usually don’t develop a long-term coaching relationship. This type of executive coaching works well to help solve a specific career problem or crisis, but doesn’t allow for longer-term leadership development and progress.


What is Mid-Level Coaching?

This coaching style has been popular for a long time and has been the butt of plotlines and jokes across popular media for decades. With phrases like “Leadership Seminars” and “Success workshops” this coaching style widens its target demographics and focuses on the middle to upper-level management. From directors to the executive suite, mid-level coaching often takes place in groups and often follows the same ideas as executive coaching, but brings in a coach from outside the organization to offer help.

The goal of most mid-level coaching opportunities is to break down the boundaries that upper-level management places on themselves through work culture, stress, career style, and more. It is a calculated and coordinated second opinion that looks to improve decision-making, flexibility, and leadership skills.

These phrases and uses for Mid-Level coaches seem as vague as Executive Coaching, but it is far from it. The nebulousness of on-demand coaching comes from its large array of tools and uses. However, the cost typically associated with this type of leadership coaching is significant which makes it incredibly difficult to scale and does not offer the same impact that many get from executive coaching.

What is Micro-Coaching by Cloverleaf?

Cloverleaf’s coaching style finds its success in the digital nature of most modern businesses where new technologies combined with teamwork are the driver’s of a business’ success. Micro-coaching or continuous micro-coaching or Automated Coaching™ is the use of weekly, daily, hourly, or continual coaching in micro-doses. Think of it as small snippets of helpful information to optimize the day for success and increase the daily takeaway.

Micro-coaching, like a digital business, thrives on algorithms and data. Cloverleaf personalizes its professional development through personality tests like the Enneagram, DISC, Energy Rhythm surveys, Strengths Finder, and other metrics. These suggestions provide answers and integrate team-related content into its coaching sessions. 

This small tweak to the traditional model of coaching offers new approaches for team collaboration and employee development. By providing team analysis, Cloverleaf can take the Enneagram and DISC of each member and plot them on charts to better visualize how each member learns, works, rests, and creates, allowing for a more agile and high-performing team.

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One of the most challenging things about being a new manager are the moments we have to have conversations we wish would…have themselves. Going from boss to coach means difficult conversations are an opportunity for growth; for you AND the team member. You will learn more about conflict resolution from the tough conversations than from the easy ones.

How do you learn to have difficult conversations? You have to have them. You have to be willing to be uncomfortable, make mistakes, and learn from them.

Why Do We Hate Difficult Conversations?

We all arrive in our roles bringing our entire lives up until this moment. The environments we grew up in shape our view of how to communicate, how to interact with conflict (or how to avoid it) and how to empathize. 

We don’t teach kids in school all of these crucial conflict management skills. No offense to your favorite math teacher, but perhaps some communication skills could have gotten as much air time as the isosceles triangle?

The adults we become then show up in the workforce with varied viewpoints and have to magically know how to navigate these difficult situations. We hate difficult conversations because we:

  • Don’t have the skills to navigate them.
  • Don’t want to hurt someone’s feelings.
  • Have grown accustomed to avoiding conflict. 

There’s actually a huge fallout to avoiding these conversations. According to Bravely, 70% of employees are avoiding difficult conversations with their boss, colleagues, or direct reports. This actually costs companies money, time, and employee engagement

Types of difficult conversations

Maybe you’ve not come across a difficult situation just yet, but let’s go dive into the deep end and make sure you are ready for these types of conversations:

Addressing differing perspectives and workstyles

  • These can be minor and based on interpersonal reasons or even work-specific perspectives that need to be ironed out.
  • An ongoing discomfort in your relationship with a team member (i.e. increased misunderstandings, tension, etc).

Identifying a workplace behavior that has a negative impact

  • You’ve got a super start on your team, but they tend to roll in Monday morning sharing about their weekend and are TMI gold medalists. Some team members feel a little uncomfortable and before it gets worse, you’ve got to address it. 
  • You have a team member who has attendance or lateness issues.
  • A team member hasn’t been pulling their weight.

Managing conflict between two team members

  • Two team members regularly disagree during team meetings causing discomfort for the team and delaying team action. 
  • There’s been an actual incident in the workplace of conflict that must be addressed ASAP.
  • A project is stalled because of conflict between co-workers.

Having to fire someone

  • Negative performance has been a pattern and after all appropriate action has been taken according to HR. You have to let the person go. 
  • Budget cuts or layoffs are impacting the company and a person’s position is being eliminated. 

Starting Difficult Conversations

The reality is these types of conversations usually cannot wait. The impact of waiting can make the impact even worse for the individual, your team and yes…you. Similarly with giving feedback, how you START the conversation can really set the tone for a productive face-to-face interaction. Here’s some conversation starters that help to level the playing field as you approach a conflict situation:

  • “There’s something I think we should discuss that will help improve our working relationship.”
  • “I’d like to talk about ____________ with you, but first I’d like to get your point of view.”
  • “I think we have different perspectives about ____________. I’d like to understand how you are thinking about it. 
  • “I’d like to see if we can come to a mutual understanding regarding___________. I really want to understand where you are coming from and also share my perspective.”

These difficult conversation starters help to interrupt fear and make it clear that this will be an exchange. Notice there is no judgment about the differences that may be present. This is part of becoming a good leader. Embracing that there are people who have valid perspectives that you may not agree with and understand is critical to being able to create mutual respect as you collaborate and lead others.

Difficult Conversation Planning Strategies

For all you color coded planners out there, YES you can plan for a difficult conversation. However you don’t want to OVERPLAN. Let some of it be organic. It’s tough to trust yourself but remember you can always criticize yourself with some self-deprecating humor later with a friend. Here’s a helpful guide to preparing for these conversations:

  1. Determine the desired outcomes from the conversation, for YOU and the team member. 
  2. Pick your conversation opener. Don’t overscript it, but have a general idea.
  3. Remember to use your active listening skills to better understand the person’s point of view, even if you don’t agree.
  4. What are the MOST important things you need to get across?
  5. What information do you need (if any) to support the conversation?
  6. Anticipate some possible responses and consider how you will handle each one. This is not supposed to freak you out, it’s just to give you some batting practice for the big game.
  7. What is the BEST case scenario? (Yes, let’s get positive going into this. We often go to a place of gloom and doom, making crucial conversations like this more difficult than they have to be.)
  8. What are the next steps you need to communicate in conversation (i.e. does this conversation require any follow up?

Remember our FEAR about these challenging conversations is usually bigger than the actual conversation. You will often let out a huge sigh of relief after you have one, so remind yourself of the COST of waiting. Go all Nike on this one and just DO IT!

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When you watch your favorite sports team come from behind and win a championship game, there is usually all sorts of celebrating, popping champagne, and visible explosive excitement. The air is filled with the energy of what is possible when a group of people, ALL committed to the same end goal, use teamwork to succeed.

Leading a team towards high collective performance goes beyond managing individual members. It’s more than meeting a common goal or completing tasks. Learning the leadership skills that can envision something greater than oneself takes courage, insight, solid decision-making, and the willingness to challenge yourself.

But don’t let this grand vision freak you out. Though you’ve just started in your role as a new manager, the only difference between a newbie and a champion is PRACTICE.

What is a high performing team?

So what makes a high performing team? Is it just meeting tangible business goals? Do team members all have to like each other?

Patrick Lencioni, basically the Godfather of high performing teams comments “Not finance. Not strategy. Not technology. It is teamwork that remains the ultimate competitive advantage, both because it is so powerful and so rare.”

Lencioni outlines the clear things that high performing teams do…and the dysfunctions that plague the underperforming teams of the world.

A high performing team does some critical things that give them a competitive advantage. Here are some characteristics of high performing teams:

  • They build trust.

  • They are not afraid of conflict.

  • They commit together and stay the course.

  • They hold each other accountable.

  • They keep their eyes on the end results.

In the beginning… 

As you get started what does this mean for you? First, have some patience. You aren’t going to establish all of this overnight. If there is one thing we forget it is that human beings are not devices. We don’t just get updated operating systems to replace the previous version. We are living, breathing, complicated beings. When you put those complicated beings in GROUPS it gets even messier. 

The ONLY thing you have to focus on at the start is building relationships.

Building relationships with each of your team members and facilitating the relationships between the entire team is a key part of building a more effective team. Relationships make ALL Of this possible. This means being yourself and allowing others to be themselves.

Just get to know the humans. Start there. Allow for the team with you at the helm to organically form itself. 

And pay attention. LISTEN. LISTEN. LISTEN. Listening is half your strategy. Listening to what people are saying…and not saying, will help you know how to proceed.

Managing conflict so it doesn’t get personal

One of the messiest things about high performing teams where it SEEMS like something is wrong is conflict. The most successful teams survive conflict because they do it with respect. 

Respectful conflict doesn’t get down and dirty. High performing teams can remain focused on the conflict at hand without resorting to personal attacks, over the top emotions, or behavior that isn’t appropriate for the workplace. Successful teams ALLOW time for this type of conflict.

Did we just say ALLOW for conflict? YES. We did. If you avoid conflict, be prepared to be uncomfortable. This is not the end of the world. It’s not like that terrible dream where you show up to high school late to take your final exams and forget your clothes. It just means we have to be ok with things NOT always being ok.

Healthy conflict generates better ideas, unearths problems in team dynamics that need solving, and can ultimately fuel innovation. So buckle up and make conflict your friend.

Strategies for building high performing teams

While you’re focusing on building those relationships, here are some strategies for strengthening your team to be one of the best.

  1. Create the space for teams to bond over non-work topics. Yes, there’s actually research on this. Whether it’s allowing some quick sharing on a Monday morning huddle or all going to an escape room together, great team leaders allow the humans to actually be humans…together.

  2. Try Lencioni’s Team Effectiveness Exercise. This is basically real-time, constructive feedback that your team gives to one another to hold each other accountable. You just need about one hour, but it’s incredibly simple and worth it. 

  3. Track team goals. Make sure there is some structure to track team goals. Whether it’s built into your company practices or you just whip up a spreadsheet, track away.

  4. Keep notes on trends that you notice. Does Joe talk a lot and take over? Is Sarah afraid to speak up in meetings? Start to jot down your observations and design micro-actions around them. For example, ask Sarah a question directly in a group meeting rather than open it up to the entire group.

Developing and leading a high performing team takes time, attention, and diligence. Whatever consistent best practices you can install into your own team operating system, do that. If something works, keep doing it. When something tanks, toss it. Remember, you are your team’s GPS. Sometimes you will change routes because of a traffic jam ahead, but ultimately everyone will reach their destination – together.

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If you’re a leader ready to learn practical management skills that utilize coaching to develop your team, check out the Boss To Coach Playbook.

About Stephanie Licata

With more than two decades of leadership and management experience, Stephanie Licata is a skilled professional coach, adult learning specialist, consultant and speaker. She has trained thousands of leaders and managers in the art and science of coaching as part of large-scale projects to develop coaching cultures within organizations. Stephanie received her professional coaching certification from New York University, and is also certified at the ACC level with the International Coaching Federation. She holds a BS in counseling and a Masters in Organizational Psychology from Columbia University.

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So what is coaching? There’s a lot of definitions out there. The way we think about coaching is there’s three key elements. One, there’s perspective. There’s someone that sits outside of your day-to-day experience that really is able to bring an outside perspective. Second element is a spark, something that ignites change moving from where you’re at today to kind of a new reality. And then the third element is action, the development component of it. So really three elements: perspective, that spark that ignites the change, and the third is achieving the best outcomes that you want for yourself.

We’re often asked, what’s the difference between coaching, mentoring, consulting, or maybe even counseling? And the way we think about that is the coach is a the thinking partner. They ask questions that lead you to self-discovery. That concept of being a partner means that they’re in it with you, not necessarily to lead or direct you and give you the answers, but more so to lead you on that path of self discovery. Three really distinct use cases for all three of those, not interchangeable. And each situation may require a mentor versus a coach or vice versa. They’re not mutually exclusive and they can be used in conjunction with each other to really support or further the learning and development process

How has coaching changed over the last few decades? Historically, coaching has been seen as a negative. I remember when I started my career, if you were being coached, that meant there was a performance issue. And that has been the historical view of coaching. You might be asking yourself, why is there suddenly an explosion of people who are entering the coaching field or have the name coach in their title? Largely that’s because there’s been a shift in how coaching is perceived in the marketplace. It’s less about the negative and working on problems and performance. Now, it’s seen as a great tool for personal and professional development. And I think as younger workers enter the workforce, the focus is more on continuous learning and continuous development. Coaching is a great tool for that.

Maybe you’ve heard the term “democratizing coaching”. How do we provide access to coaching to everyone in the organization? Coaching has primarily only been accessible to those in the top five to 10% in the organization, typically C-suite, senior and mid-level managers. If we really want to create a culture of coaching, we need to expand access to coaching to everyone in the organization. That investment seems daunting or not cost-effective. Cloverleaf is bringing Automated Coaching™ into the flow of work. This is helpful not just to expand access to coaching to everyone in the organization, but also it’s important to sustain the work that individual coaches are doing with their coaching clients when they’re not around. Typical coaching engagements are once every two weeks, once a month. What happens when that coach isn’t around? Automated Coaching™ can be the answer to bring additional facilitation and resources into the tools where clients are engaging and interacting with each other.

Often we get asked, how do we create a culture of coaching in our organization, or how do we create coaching at scale? The way we approach this is through a layered coaching concept. Obviously you can’t provide an individual one-on-one coach to everyone in the organization, but there are three key ways to creating coaching at scale across your organization.

The first, facilitated coaching. This is what we typically think of as coaching today, with either one-on-one or group facilitated conversations. In this case, a human coach works alongside these groups or individuals. The second type is on-demand coaching. This is, “Hey, I have a question.” I need access to resources to help guide us to the answers. That can come in a lot of different forms. That might look like behavioral assessment. It could be learning content. And then the third way is where Cloverleaf excels, which is Automated Coaching™. Delivering regular coaching nudges within in the flow of work. That can be accessible to everyone in the organization. There’s kind of a common framework. Cloverleaf supports all three types of coaching. We believe that every type creates a culture of coaching or coaching at scale.

Why coaching? Coaching solves a lot of team and individual employee problems. One of the common themes is interpersonal challenges. This interactivity between coworkers or team members, it shows up in a lot of different formats. What we know is that a third of a manager’s time is spent dealing with conflict. Less than a half of managers feel comfortable communicating effectively with their team members. A recent study with college students over the last three decades indicates that there’s been a 40% decline in empathy. These are all larger macro trends that point to interpersonal challenges in the workplace. Coaching is a great solution for that, especially in an Automated Coaching™ format in the tools that you use every day, how we bring together our insight into how people work.

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We’re often asked, “What’s the difference between coaching, mentoring, and consulting?”. A coach is a thinking partner. They ask questions that lead you to self-discovery. They are not leading or directing you to the answers but helping you along the path of self-discovery.

A mentor is a guide. Someone who’s been there before. They’ve walked the road and they’re sharing their personal experiences. They lay out a roadmap. Choosing to walk that path is up to you.

A consultant is just an expert. They’re someone that has looked at the situation from all sides. They have expertise in the specific challenge and will give you that knowledge to support you.

Each approach has a distinct use case. They are not interchangeable, and each situation needs a different expert. They are not mutually exclusive and can be used in conjunction with each other to support the learning and development process.

At Cloverleaf, we believe in coaching for everyone. Learn more about coaching and why it’s important

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