3 Phases of a Successful Coaching Relationship

It’s often assumed that when you lead a team you have an inherent responsibility to coach your people. That makes perfect sense in an ideal world, however in reality can be riddled with pitfalls. Most leaders are not actually trained or have developed the necessary skills to coach others. Coach training programs typically involve 1+ years of rigorous training sessions under a mentor. Not all leaders have the time, resources or know-how to locate and pursue these programs. Another pitfall comes is recognizing whether your team and potential people even want coaching from you. It would make sense that team members would desire coaching for their professional development, and leaders need to know how to create the environment for a successful coaching relationship to be formed.

Leaders stepping into the role of coach is pivotal to the continued growth of a successful team. A terrific example of this is Microsoft. The Harvard Business Review article, The Leader as Coach, discussed the shift Microsoft made from the command-and-control culture of old management practices that hampered cross-divisional collaboration. Under the direction of CEO, Satya Nadella, leaders adopted a coaching model and were encouraged to facilitate problem solving, ask questions, offer guidance, and foster employee development without making judgments.

Nadella accomplished this with the assistance of his leadership team including Jean-Phillipe Courtois, who took over Microsoft’s global sales, marketing and operations. The move to a coaching culture started when Microsoft moved to a cloud-first strategy. As the article shares, “The fundamental economics of cloud computing are based on the premise that customers will pay only for the resources they use (how long a server is utilized, say, or how much data bandwidth is being consumed). With revenue growth now depending more heavily on consumption of Microsoft’s offerings, everyone at the company had to become adept at having conversations in which they could learn what they did not already know—how to serve the unmet needs of their customers. And with the availability of powerful digital tools that provided everyone with real-time data on key metrics, it no longer made sense for managers to spend their time monitoring and controlling employees. So, after a restructuring effort aimed at giving Microsoft’s sales teams the right technical and industry skills to accompany corporate customers as they moved to the cloud, Courtois followed up with workshops, tools, and an online course designed to help the company’s managers develop a coaching style of leadership.”

“’If we want to get the transformation all the way through the organization,” he told us, “our biggest challenge is to reboot our people managers. ‘People manager’ is a job. You’re not just a sales manager, where you have a quota, a territory, customers, partners, and goals to achieve. You’re actually someone whose mission it is to pick, grow, and motivate the best capabilities to build customer success.’”

Coaching is a process, not an event, and having a framework for supplying overall coaching opportunities is critical. There are three phases of a coaching framework necessary at the onset of a coaching relationship to ensure success. These are Contracting, Planning and Developing.


When you’re beginning to coach someone, which may mean developing a brand-new relationship, or bringing the element of coaching into an existing relationship, you need to clearly set up the parameters of the coaching relationship.

First, define for the person you will be coaching what exactly coaching is and clarify what it is not. Demonstrate how coaching is different from training, counseling, mentoring and consulting. These distinctions are important because they are easily confused with one another. People may enter the coaching relationship expecting you to just tell them what to do or to start teaching them. That’s perfectly fine, however it’s not coaching. Being clear expectations at the onset sets the stage for the entirety of the coaching relationship.

Examine the level of willingness and commitment of the person being coached and stay in tune with this as time progresses. Someone may initially say, “This is amazing. I’ve been looking for this my whole career. I’m on board. Sign me up.” Then after a time it may turn out that they lack the drive, attitude or follow-through and are not yet coachable.

As the coach, you need to create a safe space for the person being coached. They need to know that what they share with you is confidential, and you may need to draw boundaries around that confidentiality, especially if you are that person’s boss. Make sure you sit down with Human Resources beforehand and verify the guidelines around confidentiality and what you can legally hold as confidential and what you cannot. Everything discussed within those boundaries is confidential and you may need to define what happens if those boundaries are breached.

Set up working agreements for your coaching. Begin by answering these questions: How often are you going to meet? What platform will you use for coaching (e.g. Zoom, Teams, phone, etc.)? How much time are you going to spend in these meetings? Will coaching be in a formal or informal setting? In a formal setting, you might decide on a regimented structure, “We’re meeting every other week, and we are going to coach.” In a more informal setting, the parameters might be more laissez-faire, “We’re going to meet every month, we’re going to be talking about your development, and as part of it, there will be coaching.” Whatever you decide, the important thing is that both parties are clear on the structure of the arrangement and expectation of each coaching session.

Make sure your coaching sessions are separate from one-on-one update meetings

These are some general “rules of the road” that should be understood by both parties:

  • The person being coached drives the relationship and guides the direction of the coaching, based on their goals and priorities, their “why,” and their reason for wanting to be coached.
  • Coaching is a partnership based on honesty. If you pushed or prodded too hard, or not enough, it’s up to the person to tell you so.
  • Coaching may be uncomfortable. Its purpose is to help a person grow and develop, and sometimes that’s difficult or even painful. Growing pains are okay, because you are both committed to the process and to the person’s development.
  • The coaching sessions may include: developmental, brainstorming, a way to uncover the real issues and how they can be solved, a place for acknowledgement and support, and a place for truth-telling by both parties.
  • Coaching is permission-based. Permission will be asked to coach in the moment, and no opinions or direct feedback from the coach will be given unless requested.
  • At the end of each session the person will determine the actions to take to which the coach will hold them accountable.


This is a checklist you can run through before each coaching session:

  • For the coach, review your notes from the previous session, and make a short list of areas to follow up on.
  • It’s ideal to have the person send you an email before each session specifying the area(s) they want to discuss. It may be helpful to send them some questions to use for this purpose, such as: What have I accomplished since our last session? What didn’t I get done that I intended to? What challenges am I facing? What opportunities are available to me right now? How can I best utilize our coaching session?
  • Review their initial goals and commitments as context for what you continue to coach them later.


The development phase is time spent actually conducting the coaching. Here are strategies to keep in mind during your sessions:

  • Establish rapport. Find common ground to put the person at ease.
  • Within each session, review successes to date. It assists the person to move forward when they can witness their own momentum.
  • Take notes—this helps you listen better and assists with follow up.
  • Be aware of preconceived notions you may have about the other person and acknowledge and filter them
  • Be mindful of your own triggers. Remember, you too are human and the person may trigger a reaction in you. Asking a question will move you out of your reactive state. Make a note to journal after your session to curiously inquire about what activated you.
  • Lean into that curiosity, inquiry and empathy. These three skills are critical for you to learn and utilize as a coach.
  • End each session by reviewing what the person is doing next and continuing to thank them for taking on doing the work that you did in your coaching session. Participating in a coaching relationship is a courageous act and having the ability to acknowledge your person for their effort and results is critical.

By setting up a successful coaching framework and environment upfront, coaches can establish a culture within an organization that fosters learning and encourages all people to grow, expand and thrive.

Esther Weinberg is the Chief Leadership Development Officer and Founder of The Ready Zone. To dive deeper into the ideas and strategies offered in this article, complete our Needs Assessment and we’ll schedule time to connect. In the meantime, download our FREE eBook – “Better Leaders. Better People. Better Results. Six Eye-Opening Strategies to Thrive Through Change You Did Not Ask For