This letter is part 3 of a series on coaching work that I've been doing with Kai Davis. If you haven't already, you may want to start with part 1 and part 2.

Shortly after I started my role as Product Manager at Moraware (about 8 months ago), I started another year of coaching with Kai. This year, we decided to break up the year into a series of 3-month chunks, each with a specific theme to help me be more productive – and each based on a specific book. 

The first 3 months, we focused on the 12-week year. The summary is that 12 weeks is the perfect unit of time for strategic planning (a year is just too much and a month isn't quite enough). Since beginning that process with Kai, I have gone from being pretty bad at personal planning to quite good at it. Now I have a regular rhythm of planning on a daily, weekly, and 12-week year basis. I’ll definitely write more about the 12-week year soon.

The next 3 months or "12-week year," we focused on Start with Why and ONE Thing. This work helped me recognize how easily I get pulled in different directions and how to restore focus on my desired direction. This was surprisingly challenging for me, and I'm still discovering ways that I struggle here.  

This 12-week year, I’m focused on adopting the practices prescribed in Deep Work. This has been all about structuring my day to support my best thinking and avoid multi-tasking. Again, I’m thrilled with the results. I find that I’m getting more rest, doing better work, and getting more work done. That’s pretty awesome.

Kai has been my secret weapon the last 2 years, but I don’t want to keep him a secret. I want everybody who's reaching for more in their career to consider getting a coach.

What to look for in a coach

Since I'm a big fan of coaching, it's probably not surprising that I also have strong opinions about what makes a good coach. I assume that there are personal preferences here, so the perfect coach for me might not be the perfect coach for you … but here are a couple of key qualities to consider.

In my opinion, the number one thing to look for in a coach is the ability to understand the way you communicate without you having to translate. 

Whenever I say something to Kai, he always understands me, even if my thoughts are only partially formed. That’s the killer feature of a great coach. We're always reaching for the next thing when we work together – that's the whole point of coaching! We can go so much faster because Kai understands the way I think and the way I communicate. 

The other important aspect of coaching is context. Generally speaking, Kai is familiar with the kinds of things I want to accomplish in my career. That doesn't mean he's a product manager – Kai's not on the same career path as I am – but he's worked with enough SaaS companies that he knows what a product manager is, and he understands very clearly the value I bring to my employer. It would be hard to work with someone who didn't understand my role.

More specifically, Kai knows me. Because we've been working together for a couple of years – and he knows quite specifically what I'm working on at any given time – I can send him a quick message on Slack and get a super helpful response – I don't have to keep establishing the context with him. That persistent personal context is a big advantage of working with a coach compared to asking a friend for help once in a while.

If you’re looking for a career or business coach, consider reaching out to Kai! His bread and better is helping freelance professionals, so if you describe yourself as a freelancer, you should definitely sign up for his mailing list and see if his ideas resonate with you. He also has some structured group programs that offer similar benefits to coaching but might be a better fit for you.

Thank you again, Kai, for all your help these last 2 years. You have made a significant impact on my life, and I will forever be grateful.

As I mentioned in my last letter, sometimes it’s useful to hire a coach to help with planning and the Big Picture, so that you can focus on execution. A couple of years ago, I decided to do exactly that with my career. 

I was feeling stagnant at work – rudderless – when I struck up a conversation with Kai Davis. He’s super nice and helpful, and eventually, he suggested I try a 3-month program he had just started to help people in my situation. For many of his clients, he called it “business coaching,” but for me, we called it “career coaching.”

Kai is kind of like a therapist who focuses on work stuff more than personal stuff. He’s a great listener, and he has a remarkable knack for asking the key questions that make you think about what direction you want to go.

When we started, Kai helped me remember where I want to go with my career and focus on the steps that would help me get there. Ultimately, I want to create a valuable business before I retire. 

This would be easy if I didn’t need money. I could quit my job, do customer discovery until I found an expensive problem to fix, and then fix it. Simple.

But I do need money. My wife and I have a 16-year-old son. Gus is my startup, and I don’t want to change our standard of living, at least not until he’s launched.

Thankfully, I have a good job with a good company. Like most people, I need to provide value for my employer each day, but I’d like to enjoy it as much as possible – and do it in a way that sets me up for future success as well.

In that first 3-month engagement, Kai helped me focus on themes related to the value I provided for Moraware at the time, especially the things I liked doing best. How can I do more of those things to bring more value while doing more of what I like? What do I also need to do outside of my day job to set me up for future success?

After 3 months of Kai’s coaching, I already felt better, and I was performing better at work, too. So I signed up for a full year of his coaching. 

A lot happened in that year. I spent about 9 months of it becoming the manager of the support team – I dove into that role, and while I am very proud of the work I did, I spent a lot of time analyzing the work with my family and Kai, and I ultimately decided it wasn’t a good long-term fit for me. First I had to be honest with myself about this, and then I approached Moraware, asking to switch to the development team from the customer team. I assumed it was time to be a full-time programmer again.

Ted, our CTO, had something else in mind. Moraware had grown to the point where we needed a dedicated product manager. The hardest part of the job is obtaining all the context related to our product and our customers. I already had that. As Ted saw the role, it was then about “taking all the squishy ideas we want to build and unsquishing them so that our developers can actually code them.” I never considered being a product manager before, but after talking it through, we both thought I’d be good at it. It turned out to be a perfect fit.

I would not have been prepared for this opportunity without Kai’s career coaching. There’s a good chance I would have assumed I had to leave Moraware to move my career forward. Instead, Kai was a neutral party that helped me analyze all my options and decide on a flexible course of action that allowed for the perfect opportunity to present itself. 

As I became more and more confident of my long-term plans from working with Kai, it allowed me to focus on short-term execution, even when it wasn’t my favorite thing to do. Sometimes you just gotta do the work. It's a whole lot easier to do that when you're confident of the plan.

Thanks to Kai, I developed a solid grasp of my strengths and how they applied to being Product Manager at Moraware, a role I had never previously considered. In this case, the ability to solve problems, talk with customers, and know everything about the product is a powerful combination – and coding experience is certainly handy, even though I’m not coding. 

Because I understood where I was going, I could see how being a product manager would help me get there. So far, it's worked out even better than I expected – I love being a product manager! It’s the perfect role for me. How did I not know this earlier?!

Again, I credit Kai for helping me be prepared when the opportunity presented itself. Thanks, Kai!

Next week, I'll dig deeper into the specific coaching work we've been doing since I became Product Manager for Moraware – and I'll share my #1 tip for choosing the right coach for you. If you have questions about coaching before then, email me.