9 Common Lessons from Coaching Individuals and Organizations

I get to work with individuals and organizations to help them realize their fullest potential. For organizations, this comes in the form of facilitating or co-facilitating leadership retreats, curriculum workshops, and strategic planning. For individuals, this comes in the format of leadership and executive coaching with clients including college presidents, CFOs of non-profits, and independent scholars and activists. Although the details of what I discuss with clients is confidential, I wanted to share some common lessons in these conversations as they might benefit others as well.

1. Essentialism

Setting priorities is one of the primary solutions that both individuals and organizations identify to move them forward. If you feel busy once in a while, it is likely situational. However, if you feel busy all the time, then it is likely because you have an inability to prioritize your own life. And when you don’t prioritize your own life, everyone else will. How can we do less, so that we can be more? How do we weed the garden of our own life? How can you apply the Pareto principle? Author Greg McKeown explores all of this in his book Essentialism: The Disciplined Pursuit of Less. I recommend it highly and often.

2. Meditation

Being more present or mindful is something most individuals I work with are seeking. Meditation, of one kind or another, is a common practice that individuals want to integrate into their lives. Meditation has been proven through thousands of scientific studies to have many benefits. There are many different ways to meditate, tools and apps to assist you, and framing to help you stick to it.

3. Handle Your Inner Critic

We all have that voice in our head that doubts us and questions us. “Why would they listen to you?” “You’ll never reach that goal.” Some folks refer to this as imposter syndrome, as though it is something that afflicts some of us. In reality, the inner critic is a part of the human condition. As Brené Brown says, the inner critic voice can come in many forms but it all boils down to, “You are not good enough.” Recognizing this voice and learning to how to handle it is a central part of how I begin all of my coaching. Usually, the best strategy is to recognize that voice, externalize it, and bypass it. Occasionally, it is a voice to be engaged. Knowing the difference and developing strategies for both are very powerful tools.

4. Don’t Make It a 22 Hour Piñata

When we really sit back and take a look, we are often the biggest obstacles in our own way. I talk about this short piece by Allison Vaillancourt often with individuals and organizations. What are the things that we make into a much bigger deal than they need to be? How do we avoid this? What is the simplest possible structure or solution to our problems? It is amazing how the “shoulds” can get us. Taking a little bit of time, getting some perspective, and really considering what needs to be done and how can save us significantly.

5. Purpose Before Action

As Simon Sinek has professed, “Start with Why.” If we don’t know why we are working on this project or pursuing that goal or leading this team or raising these kids then we can’t do a great job at it. We especially need to know why, so that when things don’t go as planned (and when do they ever?) we can improvise and still be moving toward our purpose. Most people feel that they have a sense of purpose, but unless you can write it down on an index card it can’t be good guidance for day to day decisions. I help my clients get clear about their purpose and work with them to learn how to consult their purpose to live on purpose.

6. Sharpen the Saw

This is Steven Covey’s 7th habit of highly effective people. You’ve got to perfect your instrument. If you invest the time in sharpening your saw, you can actually save time overall as you cut down the tree. In today’s day and age our most important instrument is us. When we take time to really take care of ourselves and prioritize our well-being we increase our creativity, productivity, and clear thinking. Determining what regular routines help them be at their best and sticking to them is often obvious to know and transformative to do.

7. The Middle Path or Healthy Non-Attachment

I often am reminding individuals and organizations wrestling with really difficult problems, that they might be better off if they cared a little bit less. At first, many are shocked (or appalled) because they are so committed and passionate about the issue, the people, or the cause that to suggest that they care a little bit less feels like an affront to their values. However, I’m not suggesting that they don’t care at all.  I am suggesting that caring too much is getting in their way of being able to see new possibilities and solutions. I’m suggesting practicing what Buddhist’s would describe as non-attachment or the “the middle path.”

On one hand, we have the path of caring too much. On the other hand, we have the path of not caring at all. The middle path is the path where we hold on lightly. We keep perspective. Finding this middle path can be challenging but ultimately freeing for individuals and organizations.

8. Career Clarity

Many individuals come to coaching because they feel stuck in their current career. They have not progressed they way they felt they “should.”  What has been fascinating to me is that after deep reflection about half of my clients decide to pursue a step up (or two or three) in their career and the other half decide not to pursue that path.

For some folks, they get clarity about the bigger contributions they want to make and how they want to play a bigger game. These folks then focus on what those next career steps could be and how they are going to pursue them.

For the other half, the deep reflections leads them to realize that their career is not as important is they have felt it “should” be. For these folks they get clear that other aspects of their life are the biggest priorities. For example, a client might discover that what really matters to them is being a part of a community and the opportunity to go hiking each weekend. They might realize that their current career allows for them to live in a great place, have their weekends free, and hiking doesn’t require more money. They realize that a better career could sabotage their better life by moving away from community or taking on a job that requires lots of weekend commitments. Discovering the career path that aligns with your purpose and values and helps you live your best life is always useful. The answer is just not always moving up.

9. Connecting Their Spirituality

One of the most surprising conversations clients come to is enhancing the role of spirituality in their lives. Most clients come to coaching with very practical goals like getting a better job, being more healthy, or getting out of debt. They are often surprised that they choose to explore greater spirituality in their lives. For my clients, this is rarely moving from non-spiritual to spiritual or even embracing, changing, or being more committed to their religious practices. It is more often about bringing their spirituality into more day to day aspects of their lives. It might mean connecting their spirituality to their work or even finding spiritual guidance from a tradition outside their own religious tradition.

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