A Coaching Case Study: The Challenges of Working From Home

One of the biggest obstacles to working with a coach is simply having no frame of reference for what working with a coach is like. It seems that the majority of my clients end up telling me they wish they had started earlier and that the actual process of working with a coach was not as scary or intimidating as they thought it was going to be. To that end, I'm going to start a series where I offer some case studies of real coaching engagements I've had with real people (with identifying information removed, obviously).

The relevant information for this case is that I'm working with somebody who is transitioning from a traditional 9-to-5 office job to 4 days a week of telecommuting. He's having troubles making this transition to working from home dealing particularly with distraction, lack of productivity, and procrastination. He thought it was going to be an awesome change to his life but now he's wondering if he made a huge mistake.

Here is what our coaching process looked like:

  • Our first session was centered on building rapport and me learning as much as possible about the client. He filled out some paperwork ahead of time to help get me up to speed so we didn't have to spend a ton of time with background information.
  • In addition to building rapport, we spend most of the session talking about why he pushed for this change in work arrangement and what his vision was for how it would change his work and life. I left him with a homework assignment to complete before our next session which involved writing about what being a successful telecommuter might look and feel like to him.
  • In our second session we talked about his homework assignment and really solidified what he's shooting for. We then spent the rest of the time doing a values elicitation exercise to help him get super clear on his underlying values. Once his values were extremely clear to him we started the process of identifying where his current behaviors were falling short of the values he holds. We also identified where in his life and work his behaviors and values are aligned. We started creating a list as we ran out of time in the session. His homework was to finish creating the list.
  • We started the third session by looking at the list of mismatches between his values and his behaviors. I had him pick the one that seemed the most important. He homed in on the idea of a lack of discipline in the way he has treated his working from home even though Discipline is one of the values that emerged from his values elucidation. We started talking about the changes he would need to make to bring more discipline into his work. We brainstormed a bunch together and I asked him to pick just one to focus on for the next week. He decided that he wanted to try a Morning Start Up Routine that involves planning his upcoming day, writing in his journal, and completing 20 minutes of his most important work task before checking email or any social networks.
  • I sent him an email a couple days later to see how things are going and offer some support.
  • We started our fourth session talking about how the Morning Start Up Routine experiment went. He found a decent amount of success when he did the routine but forgot to do it a couple of days. We talked about how he can prevent himself from forgetting to do it in the future and he decided to add it as a recurring task on his calendar and he made a little note to stick to the bulletin board in his office. He decided to try adding on an End of Day Routine experiment and we talked about how he could best install that habit given what he learned from the Morning Start Up Routine experiment.
  • Moving into our fifth and final session he felt pretty good about the two experiments he had done so far. In order to make sure progress was going to continue after this final coaching engagement we spent most of the session creating a list of other experiments he can do to reduce the gaps between his daily behaviors and the values we elucidated in our second session. We spent some time talking about the order in which he should tackle these and how he will judge whether he was successful. This led us into a brief discussion about the importance of self-reflection and this prompted him to add the development of a self-reflection routine into his list of experiments.
  • We finished up the final coaching session with a virtual high five and the promise to check-in after a couple months to see how everything is going and possibly consider an additional "booster" coaching engagement if he feels it's necessary.

Coaching Toward Self-Development

Across five sessions he made serious progress on tackling the productivity issues that emerged from shifting into a telecommuting role and not being used to that style of work. Most importantly, he built his capacity to self-develop by going through the process of identifying mini-experiments he could conduct by himself and then coming to conclusions about whether or not they are improving his situation. Any good coach should be able to teach his or her clients how to continue coaching themselves after the coaching engagement is completed.

Hopefully that gives you a bit of a glimpse into what a potential coaching engagement with me actually looks like. Do you have any other questions about the process of coaching? Shoot me an email ( or leave a comment.

Photo by Arlo Bates

Going Pro With Your Personal Development

I’ve always been fascinated by people who are the very best in their field. One of the most visible sets of people that fit this criteria are professional athletes. With my experience in playing and coaching ice hockey, I’ve been able to get a closer look than most at what it takes to be a professional or semi-professional athlete. These men and women have development and practice down to a science. They know what it takes to be the best they can possibly be.

You may not be playing a game in front of thousands of people or getting paid millions of dollars, but I think we can all take some lessons from the pros when it comes to our own personal development.


First of all, let’s look at how athletes practice. The first thing that most people don’t really think about is that being a professional athlete means you spend about 80% of your time practicing, training, and preparing and only about 20% of the time actually performing the skills you spend so much time practicing. We only get to see the finished product and very few of us get a look at what goes on behind the scenes. Athletes train for hours nearly every day to prepare themselves for the couple hours of performance that we all get to see. I’m not as interested in the final product as I am the work that it takes to get to that point.

Secondly, professional athletes approach their practice in a systematic way. Granted, the structure may be dictated by a coach, but no professional hockey player would just spend a practice session monkeying around without a plan (monkeying around WITH a plan, like improving stick handling skills, happens all the time, though). Practice sessions have a logical progression that allow the athlete to work on very minute skills that, when put together, equal the ability to do their job at a highly competitive level.

Now, I understand that most of us don’t have a job where we have the luxury of practicing all day and then executing our skills in front of lots of people who want to give us money. Most accountants I know don’t sit at home for eight hours practicing only to go into work for two hours in the evening. Doesn’t quite work that way in the real world. However, let’s forget about our careers and jobs right now and think about another way we are all professionals.

We’re all professional humans.

This is what we do and are every day so why not treat our personal development like the pros?

How can we go about treating our personal development in the same way pros approach their own development?


  1. Deliberately Practice: Athletes break down their practice into the various skills they need to perform. And then they break down those skills even further. Breaking complex skills into simple parts that can be practiced over and over is what separate people who do amazing things from those who don’t.

  2. Unfailingly Practice: Athletes show up for practice no matter what. I’ve gone to many a hockey practice when I was sore, tired, and didn’t feel like being there. But not going to practice isn’t even an option. It doesn’t even register into the realm of possibilities for professional athletes. You need to make a commitment to your development that goes beyond immediate gratification.

  3. Practice With a Plan: Athletes and coaches approach the development of themselves and the team with a plan. On the coaching side of things, the practices that happen at the beginning of a season are very different from those that happen at the end of the season. Have you done an audit of your own skills and abilities to see what you need to work on the most? What is happening in your daily life that would benefit the most from improving a specific ability? You can’t practice effectively without a plan.


But wait, athletes have coaches!

Seriously? You can’t make that argument when this whole website is being run by a life coach. Life coaches are to “regular people” what sports coaches are to athletes. Granted, I realize that the vast majority of people who read this blog will never hire me. I’m perfectly fine with that and will continue to write free articles for everyone to enjoy.

Let me give my quick little schpeil on how I see life coaching, though. In the past, personal development and your job went hand-in-hand. People would find a secure job and they would develop the skills necessary to move up the ranks in that job. Eventually, they’d hit a ceiling or retire with a decent pension and hopefully some savings to live off of. No need for a life coach when your employment situation was stable and your job would happily provide you with opportunities to develop the skills you need to work your way up.

But that is changing. In the new economy most of us will never have that life long job that will provide for us forever. We aren’t going to have our salary needs and our personal development needs met by our employers anymore. Instead, our personal development is going to become just that, personal. The steps that we take to improve ourselves are going to be what set us up for success in an economy where our job situation is constantly shifting with the winds of uncertainty. A job isn’t going to nurture you along anymore. You are going to have to take the initiative to improve yourself. And that’s where a life coach comes in.

But I digress.

The last argument that I can see forming on the lips of everyone reading this article is, “But athletes make tons of money and can afford to spend all their time getting better at their job! I have a job and a family and responsibilities! I can’t just sit around reading philosophy and learning another language all day!”

I worry that my answer is going to seem harsh, but I’ll take that risk. And that answer is:


Are you going to let the excuse that you’re busy and have responsibilities be the reason you don’t take control of your own life? Are you saying it’s only worth the effort to become the best person you can possibly be if you’re being showered in Benjamins? You don’t believe that and neither do I.

Sure, it’s tough to find the time to improve yourself when you have real life demands that require your time and attention. But if effective personal development was easy there wouldn't be a humongous self-help industry, I probably wouldn't be writing this article, and there would be little reward for putting in the time and effort to improve yourself.