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30. Coaching for Strategic Leaders-2: Connecting With Others Through Care and Compassion

You may have heard it said that people don’t care about what you know until they know how much you care. The starting point for a good coaching relationship or session is care and compassion. We all need human connections. These connections build trust and authenticity. Good coaching relationships are built on empathy. Empathy is your desire to see their experience through their eyes. What are they facing and what does is mean to them? As we mentioned last week, good coaching is about them and not about you. Coaching goes better when the person feels your empathy and support.

Opening any coaching relationship or conversation needs to include these three important aspects:

  • The first is care, which we have already touched on.

  • The second is confidentiality. People need to have confidence that what is shared in a coaching conversation will not be shared with others.

  • After care and confidentiality comes competence. You want to come to your coaching times with basic skills so you do no harm but can instead provide the support they need. As we said last week, these basic skills begin with asking good questions and listening well. Keep things focused on the coachee rather than on you. This means that you allow them to reflect on their journey and make their own decisions going forward rather than directing them on what they should do. Lastly, it is a commitment to professional propriety in your relationships, especially as it relates to cross-gender dynamics and confidentiality.

With each of the five coaching tools in this series we will unpack the concepts on two levels. At a higher level, we will talk about how this tool fits into the longer coaching relationship. For example, when you are connecting with a person in a new relationship, you will want to look at some bigger issues. When you are looking at connecting with a person for an individual session, the time frame is shorter.

Let’s start with the bigger issues of connecting. If you are starting a new coaching relationship, you will want to look at several topics. First, start by asking what they would like to get out of their coaching experience. Second, get some information on their background. This can include family info, work background, or anything else that seems relevant. Next, talk with them about the time frame. Would they like to do a few sessions on a particular issue, or would they like an extended time frame that might mean working through issues over several months?

Next, you might consider using an assessment during this early connection phase. You could use the Myers Briggs assessment, the DISC, StrengthFinders, or even the Enneagram. I like to say that these assessments are not perfect, but they can help you to get to know the person more quickly and help them to grow in their self-awareness. If you are looking for a place to start, offers a free Myers Briggs assessment with follow-up information. After the person sends you their profile, you can take some time to talk through what it says. Ask them what about their profile is right on and which aspects don’t sound like them. Keep this profile as you may want to refer to it at a later time.

Lastly, you can discuss any payment issues. If you are doing this for free or it is just an informal coaching conversation, this really doesn’t matter. However, if there is a fee for your time, you could let them know how much that might be and how payment will work.

When it comes to connecting in an individual coaching session, I will often start with the question, “What’s new in your world since we talked last?” I could also ask, “Has anything come up since our last session?” This provides the opportunity to connect before you dive into some deeper issues. Many times their answers are not earth-shattering. It can be just talk about work, relationships, or travels. Sometimes, however, there have been significant issues like COVID, challenges at work, or family issues that need some additional discussion.

Connecting at the beginning of a session also gives you the chance to check in on the next steps from the last session. You could say, “Last time we talked about putting your resume together for that job search. How is that going?” You want these check-ins to be supportive, so that the person does not feel bad if things have not gone well. If they have made progress, celebrate this win with them. If they have not made progress, you can take a few minutes to explore what kept them from moving forward.

As you think about next steps from these materials, think about those in your world you can connect with. Here are some examples. You can start informally with friends and family. You can connect by taking the initiative to see how they are doing and what’s going on in their lives. For more formal coaching relationships, you can ask about how this engagement might work. For example, if you would like to bring coaching into your work with your direct reports, you could sit down with them for coffee and ask them if they would like to have a coaching session or two each month. If they ask, “What would that look like?” you could say that your purpose is to provide a time when you could focus on their professional development aside from their work responsibilities. You could talk about how you want to support their growth and development but on their terms. Your goal is to help them on that journey and not to tell them what to do. I find that with many younger employees, they are often looking for opportunities to grow and develop but feel that their boss doesn’t care about this and just wants them to do more work.

I once had a person I was recruiting for a job tell me, “I really don’t want to come to your city, but if you can help me figure out how this job works, I will come.” The person ended up coming and stayed for ten years. They did. great job.. Many young adults and employees are looking for good supportive conversations that can help them to move forward.

In closing, people are looking for connections with people who care. You cannot care and connect with everyone, but there are those few people you could start with. Whether it is in a longer term relationship or just an individual session, begin by connecting with care as the starting point as you seek to help others become the best version of themselves.

If you would like a free coaching session to talk about these issues or others, feel free to contact me. My email is


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