How Coaching Works
A coach is like a co-pilot for your career.
“I am not a product of my circumstances. I am a product of my decisions.”—Steve Covey
Becoming a coach has changed me forever. My clients say it’s changed them, too.
I’ve been working as a business and career coach through my company Business Letters for several years. After 30 years working in startups and big corporations, I’ve completed hundreds of 1:1 coaching sessions with people — amazing people — helping them understand their circumstances and make better decisions.
When I started out, I wasn’t sure how coaching was supposed to work. I’d heard of “executive coaches” who I imagined as golf-playing CEO-whisperers. I knew I didn’t want to do that.
I’ve always identified with underdogs and I’m thrilled by the idea of helping people gain access to spaces they’ve felt excluded from. I want to set free some of the lessons I’ve learned and the secrets I’ve discovered while rooting around in the patriarchal vault for the last 30 years.
I welcome clients from all backgrounds. Humbly, I consider myself a specialist in trying to help level the playing field for people from marginalized communities. My clients are disproportionately women, people of color, and neurodivergent. I’m part of the queer community, and LGBTQIA+ clients should feel very safe here. All clients from any background are welcome.
After 30 years of being a people manager, I certainly know something about it. It’s not that I believe I’m the world’s greatest! One reason I started coaching is because I feel terrible about the times I’ve been a terrible manager. I want to be better, and teaching is the best way I know of to learn what you know. A desire to improve is the lone mandatory credential for leadership.
There are many kinds of coaching, and there are many kinds of coaches. If another coach says their way is better, they’re probably right. I don’t necessarily think mine is the best approach, but it is getting better all the time. My clients like it, and that’s what matters most to me.
I think it’s a pretty good way to work with people. May I tell you about it?
What is Coaching?
A client described me as a “work therapist.” That feels so accurate that, out of guilt, I immediately called my own therapist and apologized. Comparing coaching to therapy is ungenerous to those who have years of formal training, are licensed, and have Master’s or Doctorate degrees and years of on-the-job training as prerequisites. We love you, therapists!
Coaching compares well to personal fitness training. It’s time that you set aside every week (or month, or whatever) to work with an expert and to focus on yourself. Of course it’s important what you do with that time, but hiring a coach (or a trainer) is a great way to commit yourself to the process.
People who hire coaches, like those who hire trainers, are intentional about self-improvement and ready to do hard work on it. People don’t generally get coaching or training because they need it. They want to dedicate their time and the expertise of a professional to help them do even better.
People who seek out coaching are invariably amazing people. I’ve talked to other coaches, and it’s not just me. It took me a while to work this out — people who seek out the opportunity to invest in themselves are a self-selected group of high performers.
So how does the work… work? Here are some ways:
First, we set goals. Many clients have a collection of outcomes they’d like to achieve. Sometimes they come in a prioritized list. Sometimes the goals are unfocused or contradictory, so we’ll often work to straighten that out. I have learned a lot about career progression and the growth of businesses, and clients often want to learn what I know about that.
We also identify and practice skills relevant to achieving those goals. For clients looking to get hired or promoted, we work on their resume, LinkedIn profile, and their interview preparation. I have taken many from utter despairing the spectre of an interview, to calm and competent performers in just a few weeks. I work with people in many disciplines — product managers, people managers, designers, project managers, and all kinds of other professionals — to help them refine their craft.
Coaches and Mentors
There’s a distinction between a coach and a mentor. The coach of a sports team is not meant to be the greatest hitter or even able to hit a 3-point shot. A coach knows what great looks like for every position on the team. A coach knows how to get a good player to become a great player. From experience, not book learning or training, they know everything about the game. They understand all the rules, written and unwritten, when to follow them and when to break them.
That’s me!
A mentor will also do many of these things. Mentors coach, and coaches mentor. In addition to your coach, manager, and peers, it’s good to have a mentor who is closely aligned to your craft and how you practice it today. For many clients I occupy some of this role, and I help them find their own mentors as well.
Together with clients, we also measure progress. People want a roadmap or benchmark for their career or business. They’d like an honest read on how how they compare to what’s out there. I’m happy to share that, based on my experience working with so many businesses and people over the years. I use my perspective to give an honest assessment of your business or career, a realistic assessment of what comes next, and a candid prescription for what it’s going to take to get there.
How Does it, Like, Work?
It works how you need it to work.
I usually see clients for an hour every week, every other week, or each month. Mostly we meet via Zoom, some by voice. In between meetings we connect by Slack, text, and email. My client and many of my readers share a community called “Safe @ Work” which you are very welcome to join right now.
Unlimited coaching via Slack, DM, and text between meetings is 100% free. I don’t charge extra for that. I reserve the right to limit it, but I’ve never had to. I want to hear what’s happening, answering questions, reviewing/commenting on documents… contributing however I can help.
Most coaches use frameworks. Clients have told me they’re asked to fill out forms or surveys, sit through presentations, learn their “score” or “personality profile”, and complete exercises. I don’t do any of that. I’m not saying it’s bad, I’m just saying I’m not going to ask you to fill out any forms.
In our first session, we talk about what you’re looking to get out our work together. I have one thought exercise that I talk through with most clients, which I’ll tell you about in a minute. At the end of our first hour, we map out together a kind of now/next/later of what we’ll work with in the next few sessions. We’ll iterate on that each session.
Sometimes a session will happen right after something interesting or unusual has happened at work. In that case, we might toss out the agenda in order to talk about that thing, if that’s what you want. It’s your time, so it’s your agenda. I expect to hear from clients mid-week by Slack, DM, or text if anything serious comes up. I’m often found talking to clients after dinner about an unfolding drama.
Really, Though, What Goes On in the Sessions?
Every client is different.
Usually I start out asking “How’s work?” For some clients we’re working through a planned set of tasks to improve a resume, profile, or to prepare for an interview. For others, it’s an unstructured conversation about what’s happened at work.
The sessions are a safe space for you to say anything, any way you need to say it. There’s always a lot of laughing, and sometimes a little crying.
Often we start out with you telling me what’s happening at work. You’re probably asking questions like “Is this weird?” “What does this mean?” or “How should I handle this?”
A friend of mine got a coaching certification. Fascinated, I asked her what she’d learned. She said that they’re trained not to have strong opinions, points of view, or to give decisive answers to the clients’ questions. I winced and said “Well, that’s not how I do it.”
I’ll give you frank, honest answers whenever I can. Sometimes they’re not what you want to hear. I will ask a lot of questions of my own in return. Clients who are interested in working with someone who will call them on their own contradictions will feel right at home working with me.
I often suggest reading, and I might suggest you complete a writing assignment. One thought exercise I work through with almost every client is called “limiting beliefs.” Here’s how it works.
Take a piece of paper and draw a line down the center of the page. On the left side of the page, write down everything you believe is holding you back from achieving your goals. On the right side of the page, write down what you have accomplished in your career. Include significant, meaningful, recent feedback — good or bad.
The things on the left side are “limiting beliefs” and the things on the right side are called “facts.” Many people find the left list is longer and looms larger in their life than the things on the right. That’s something to meditate on. The things on the left side differ significantly from the right in that they do not actually exist. 🤔
What Are the Ground Rules?
I have five ground rules. Here they are:
Cancellation: There’s a cancellation but it’s really meant for repeat last-minute offenders. The reality is that people have to cancel or reschedule their coaching appointments and I’m happy to accommodate that whenever I can.
Confidentiality: I don’t tell anybody what you tell me, ever. This is covered in my Terms of Service. Additionally, I let every client know that if I ever write about what they tell me, I will fictionalize it to the point where you’ll never even know it was you. I don’t want you to worry that I’ll write about something you tell me. I won’t.
Boundaries: Let’s have them. You can tell me anything you want that you feel is relevant to our work together. I’m not going to get weird or offended by it. My clients have told me all kinds of stuff, so by now I can handle it. If it gets uncomfortable for me, I’ll let you know. If you have any boundaries that you want me to know about, please feel free to set them and know they’ll be respected.
Referrals: If you refer a paying client to me, you get a free coaching session. If you refer 5 paying clients to me, you get free coaching for a year.
Ask for what you need: Clients are invited to ask for help between sessions. I work with them asynchronously, informally, via Slack and email for free. I’m not going to check on you between sessions. If you ask for more than I want to provide without charge, I’ll let you know. Lapsed clients: my door is always open to you even if I haven’t seen your credit card in a while. Don’t worry about it. When I need to be paid for something, I’ll let you know.
My approach to every client is individual. I want to craft my services and our relationship around your needs. I want to give you the type of advice, feedback, or method of working together that’s most meaningful for you.
Whether I’m a work therapist or a personal business trainer, your corner man or your confidant, I want the time that we spend together to be the most meaningful hour of your week.
As I’m publishing this, I have openings for 1:1 coaching but my schedule tends to fill fast. Drop me a line if you’d like to talk. Whether or not you’re ready to start coaching now, I’m always here for you if you need to chat.