🔥 Hot Take Alert #3: The world doesn't need any more 25 year old "startup coaches"
Two exceptional coaches teach me about why people become coaches, certifications, what coaches do and don't do, and how to find the right coach for you.
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Welcome to another 🔥 Hot Take Alert 🔥 where I opine on something that I feel very strongly about and try to make it a little bit better. I plan on doing these a few times a month. I don’t expect you to agree with all of them but please keep an open mind. Or don’t. It’s your subscription.
Past 🔥 Hot Take Alerts 🔥
Last week I published the first part of my three part series on choosing your company. I plan on releasing the next part in another week or so but before then it was time to get something important off my chest.
The world does NOT need anymore 25-year-old “startup coaches.”
That’s right folks—these days you can’t navigate past two profiles on LinkedIn without coming across a newly-minted “coach.” You know the type. They have a profile extolling their 2-3 years of experience that they’ve stretched into 5 years because they worked at the radio station in college or ran a lemonade stand in high school.
Their headline includes “advisor, investor, entrepreneur, 42nd Product Manager at [hot startup].” Maybe they’ve even started a newsletter 💀. They have a professional-looking headshot with their arms crossed staring out into the distance deep in thought. They were on a team that did a thing that you might have heard of once. Or maybe not. Doesn’t really matter.
The world has exploded with coaches. There are now entire companies dedicated to helping you find one and the search for “how to find a coach” returns over 700 million entries. Wow.
And as Andy Johns said to me, we don’t need more coaches. Period.
“I would go a step further and say that not only do we not need more [coaches], but they are net negative in terms of impact. Building a highly successful startup (or becoming a highly successful person) is a path to mastery. Mastery can’t be explained to another person. I can’t become a master at serving a tennis ball because Roger Federer tells me about how he does it. I can become more proficient, but not master it via that method. Mastery requires going off road. It’s a path that can only be discovered, not taught. It’s a fundamentally solo journey of mastery through experiential knowledge. As soon as a founder copies directions provided by a coach, they have veered off the path of mastery.”
Andy has a good point and at the same time I don’t believe that all coaching is bad. The truly exceptional coaches don’t tell people what to do but help them with frameworks for decision-making.
There are some coaches who are truly gifted and have coached the titans of the tech industry—people like Bill Campbell; Jerry Colonna (who founded Reboot); or Diana Chapman and Jim Dethmer of the Conscious Leadership Group. Many hundreds more who aren’t coaches to the stars but still coach many of the executives and leaders who power our industry. Then there are thousands of others who coach the up-and-coming future generation of leaders.
And then… there is the 25 year old coach.
I don’t have anything against that age. I was once 25 and I have worked with many bright, driven, and thoughtful people who were in their mid-twenties. This isn’t a Gen Z takedown post. It’s not about age; it’s about experience.
The problem I have is that a lack of a broadly accepted definition and detail on what it means to be a truly exceptional coach has led anyone with a few hours of time on their hands to appropriate the term.
Let’s end that practice now.
To help demystify coaching I interviewed two truly exceptional coaches (including one who started at age 25!) for a deep-dive into what a coach is and isn’t, what it takes to be a great coach, how to find a coach, and how to make the most out of the relationship. This should help you sift through the “advisor, investor, entrepreneur, 42nd Product Manager at [hot startup]” and find a coach that helps you reach your potential.
Read on to learn:
Why people become coaches
The different types of coaching certifications and what they mean
The process for coaching certification and what it takes
What coaches do (and what they don’t do)
How to find the right coach for you and what to pay them
The risks of choosing the wrong coach
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Why do people become coaches?
Despite this hot take (or maybe because of it) I am a huge proponent of coaching and have benefited from it for over a decade. I’ve worked with Courtney since 2012 when I went from managing a few people to managing a team of 20+. I also recommend coaching to mentees, professional colleagues and peers, and team members that I’ve managed who I thought would benefit from an outside perspective. In all the years I’ve been coached I never stopped to ask what draws people to the profession.
For Natalie Rothfels it seems like she was born to do it:
“In hindsight, it’s become clear that I’m someone who likes digging deep with people and helping them to uncover who they are, what they actually care about, what they’re scared of, and what they’re dreaming about. I think I’ve probably had a natural predisposition towards coaching-like things for most of my life…
…I grew up in an environment where a lot of things were deeply confusing to me. I think I started asking slightly-provocative questions to try to make more sense of my world. I’m the person at the party that will ask you a very weird question and be genuinely curious about your very weird answer. I try to also genuinely answer people’s mundane questions, like “How are you doing?” by describing honestly how I’m actually doing.”
Having collaborated closely with Natalie on a few in-depth articles at Reforge I can say this describes her to a T!
Courtney Joyce shares a similar sentiment:
“I became a coach in 2011. I was actually a literacy coach in an elementary school when I switched over, but before that job, I worked in tech marketing and sports marketing for 15 years. I worked at 2 different start ups for 5 years each which does help me understand the issues that many of my clients face working in startups. It's not a requirement for a coach to have experience in the same environments as your clients, but it can be helpful to have a shared language and understanding of context.”
Having worked closely with Courtney for the last decade (and Natalie for the last year) I can say that I’ve found both passion and experience to be equally important. One of the reasons I gravitated towards working with Courtney a long time ago was that I felt like she understood me—both personally (as a parent) and professionally as a startup executive. And since coaching requires a great deal of empathy this was a big benefit to our relationship.
For those considering going into coaching I also found Natalie’s logical approach to “why” fascinating. It was her time as a Product Manager at Khan Academy that started her on the path to becoming a coach:
“I was in my first PM role at Khan Academy and had no idea WTF I was doing. People were coming to me left-right-and-center with problems. Bugs to triage, meetings to run, partner complaints to remedy, decisions to make, etc. The usual PM stuff that you just learn how to juggle and prioritize more effectively as you grow in your career. But I was struggling, and I thought…wow, I really have no idea what the answer is to any of these questions…but somehow I’m kind of…in charge? So I decided to go into a coaching program actually in support of becoming a better PM. I wanted to learn more tools for helping people get unblocked, figure out the answers themselves, and work through tough problems without me actually needing to know the answers explicitly.”
And of course you have to enjoy it. From Natalie:
“So I honestly went to the first weekend of coach training and thought, Wow, that was fun! And then I just wanted to keep doing fun things… I kept going with coaching because it was intellectually stimulating, right at the edge of my comfort zone, and also seemed to make a real difference for people. But also I just didn’t really think about it too hard. I just said “Yeah, okay, let’s do it!” I preach about decision-making a lot, but I also think it’s totally viable to have your criteria for decision-making include “Just Cause It’s Fun.”
The next email you receive could change your life. Or make you laugh. Don’t miss it!
Coaching credentials, certifications and what it takes
Passion isn’t enough and coaching is a profession where tools and frameworks can make a huge difference. I asked Natalie and Courtney about the different types of certifications that they hold and learned a lot about the process.
Both of them were trained by the Coaches Training Institute (CTI) which is now called Co-Active Training. The process is rigorous and time-consuming.
Natalie describes a process that takes about 200 hours to complete the first level of certification:
“It was a 6 month process of weekend-long workshops, and then another 6 month process of certification, which included weekly classes, coaching supervision of actual sessions, working with your own coach, developing your own paid client roster, and then eventually performing several adjudicated live coaching sessions.”
And Courtney described the same rigor:
“At CTI you spend approximately  months in a class (3 days per month) and then you move to the practical portion where you coach others under observation. This was by far the most valuable part of the program. You record coaching sessions and a certified master coach listens in and gives you feedback after each session.
You keep coaching that same person and try to grow based on the feedback from your mentor. And then in the end you go through a written and in-person exam where you coach a master coach while 2 others observe. Having real time feedback on your approach, choice of words, etc is so helpful. You also need to document a certain number of hours of coaching before you can get certified.”
What’s interesting about this is that unlike professions like therapy, social work, and even being a licensed contractor (at least in California) there isn’t a standardized credential required to become a coach. Also the types of certification and therefore the requirements are largely up to the individual training programs.
Courtney described this as the wild wild West:
“The truth is that you don't need certification to be a coach which makes the profession a bit of a wild west. Unlike therapy or social work it's not a legal requirement. I coached for 4 years before I got certified. I am so glad I did get certified because not only did I learn a lot through the process, but I feel better about my long-term prospects as a coach with some foundational knowledge.”
And this is the reason that in the world of coaching it’s important to evaluate the credentials of your prospective coach (more on that later).
Both Courtney and Natalie started with becoming Professional Certified Coaches (PCC) but there is also the International Coaching Certification provided by the International Coaching Federation (ICF) which many people consider the “gold standard” according to Courtney. It’s helpful, but not necessary:
“...many people are PCC and ICF coaches (or some are just one). I had the option to get ICF certified at the end of my PCC certification (it would have taken a bunch of paperwork and some registration funds) and in the end I decided PCC was good enough.”
Natalie went for the ICF Accreditation which requires submitting a certain number of logged hours of paid coaching and taking a competency exam based on core coaching skills. Here she describes the approach from end-to-end, including adding a supplemental training in Internal Family Systems therapy:
“Training was 200 hours, and then to become ICF-accredited you need a minimum of 100 hours of paid coaching time. With my full-time PM role, it took me about 12 months to get to 100 hours after already being certified as a CPCC (Co-Active’s credential). That panned out to be about ~8 hours a month. So from the beginning of training to certification through ICF it was about 2 years alongside a demanding full time job. I’ve supplemented my coaching credentials with training in Internal Family Systems therapy (both for individuals and couples), which I really love and has served me well for some of the self-inquiry and relational approaches above.”
Although coaching can have a therapeutic feel to it, Natalie is quick to point out that she’s not a licensed therapist:
“I do think coaches need to be really explicit and clear what kind of coaching they’re doing, and what kind of credentialing they have for that coaching. Even though I have background training in IFS, I am not a licensed therapist and I need to be explicit about that upfront.”
The journey doesn’t stop with the first 200 hours or the accreditation. There are always new skills to learn and facilitate: 360-reviews, self-inquiry, relational and leadership coaching, or even Natalie’s work training in IFS which she’s been able to bring into her coaching practice.
Both Natalie and Courtney describe a process that is rigorous, structured, and leads to a lot of hands-on experience and feedback. Knowing their learning journey, certifications and skills can also provide a window into the various types of coaching and what might work for you.
What coaches do (and what they don’t do)
As mentioned above, coaches are not therapists. Even if we treat them as such from time to time (guilty!). Coaching can be radically different from person to person both in the coaching style, the focus, and the skills they bring to the relationship. It can also evolve over time and is often steered by what the client needs.
Natalie describes a process that is “coaching-adjacent” in some ways. She can get pulled into other aspects of the business beyond 1:1 coaching:
“I coach 10-15 hours a week today, and because I work on retainer, I also end up helping folks asynchronously in more of a product-and company-building advisory capacity. Many of these things feel more coaching-adjacent (like co-facilitating this upcoming workshop on behavior change for climate-focused founders) because I’m using coaching skills, but may be developing content, facilitating an offsite, or helping develop a product strategy (none of which is explicitly coaching).”
And Courtney started her coaching career as more of a “teacher” than a coach:
“I started coaching at a consulting firm that had about 20 coaches on staff as contractors, and their brand of coaching was half-coaching and half-teaching. So when I first started coaching I was doing a lot of teaching which really isn't coaching at all. They had their own curriculum and would teach listening skills, communication skills, presentation skills, negotiation, sales basics, time management and many more. Over time I've had to un-train myself from the teaching part of coaching and focus more on true coaching which has no formal teaching or advising.”
Both indicated that this is more of the exception vs. the rule. And in my conversation with Natalie she broke down the various types of coaching she does in a very handy table. This can also be useful for you when explaining your needs to a coach.
The cells can be fluid as Natalie points out:
“It’s not important to stay in one cell – it’s important to be on the same page upfront about what cell you’re starting in, and then again when you’re moving into a different cell. I use different styles and tactics for each, but at the core I’m holding my client as my teammates: I want them to thrive and feel more connected to themselves and others in their everyday lives…at work and beyond.”
Just as the various coaching certifications and accreditations can contribute to the wild West experience, so too can the varying nature of what coaches offer their clients.
Courtney and I discussed this definition:
“I guess this is a good time to actually talk about how "coaching" is defined very differently from each coach which also adds to the wild west nature of the coaching profession. There are coaches who are more practical and do more teaching, advising, and mentoring. I know a lot of coaches who coach in their specific field (CTO coaches, CEO coaches, etc).”
My coaching practice has also changed because I am working mostly with startup companies and startup leaders. Most of this is because of my work with Reboot but I also find that this is more interesting work for me as a coach and startup life lends itself very well to coaching work (so I am seeking and saying yes to engagements with startup leaders more than engagements with larger companies).
Startups are fast paced and change quickly which often creates new and emerging issues that are great to work through in a coaching session. [editor's note: NAILED IT.] Also if the company is smaller the sphere of influence is greater. Anecdotally I've also found that startup employees are typically more engaged and invested in the company and their part in it, which also lends itself well to coaching.
The ongoing work of coaching is primarily about personal development and growth. One aspect that always stuck with me is that the coach is there to ensure you (the coachee) are successful. Sometimes that means at your current place of employment and sometimes not.
“As a coach, I am there to help my clients with their personal development and growth. There is no curriculum and I certainly don't have the answers. I always spend time at the beginning of an engagement to learn what success would look like for that person and we work towards that. But at a high level the goals are for my clients to gain more awareness about themselves and how they are showing up, and to eventually feel more in control and fulfilled in their work life.”
As part of Courtney’s inquiry process, which gives you a view into her approach to coaching, she sends a series of questions to new clients.
It’s important to understand that outside coaches aren’t accountable to your work deliverables. Unlike the coach of a sports team who is hired and fired by the owners or general manager (i.e. CEO) your coach isn’t making decisions for you. They’re also not providing you with specific content for a project you’re working on—don’t expect them to give you a Product Brief template or run you through annual planning. They can be a great resource for practicing and getting feedback on these artifacts, but only if they’ve had experience with that type of work before.
In order to establish these guardrails Courtney starts every engagement with a document that lays out what coaching is and isn’t.
One of those areas defines the differences between coaching, therapy, mentorship, and advising:
“Coaching is slightly different from therapy, advising or mentoring (although coaching can, at times, have elements of these things). Therapy spends a lot of time looking toward one’s past, whereas coaching is forward-looking and future-oriented. Advising is when a person provides specific advice based on their experience and is based in collaborative problem-solving. Mentoring and advising typically consists of a more experienced person directly guiding the mentee through an experience that the mentor has already been through. A coach does not always have experience in the work areas of the coachee.”
And Natalie is clear on what is and is not part of the job:
“Unless we’ve designed a contract as such upfront, I’m not producing content or materials for you or your company, or running you through a cohort-based course. I’m not giving you access to an exclusive community that will change your life. I’m also not on your cap table (yet 😉)”
Recognizing what coaching is and what it isn’t is critical to engaging with the right person given the myriad of certifications, specializations and personality-types out there. This brings us to our final step: evaluation.
How to find the right coach for you (and what to pay them)
Treat finding a coach like you would hiring a new team member. As I’ve laid out in previous posts, you have to do your pre-work first.
Natalie calls this “looking for internal clarity” and she provided a great set of questions to ask yourself to get started. I’ve bucketed them into “why, what and how much” questions:
Once you’ve done your own internal reflection on the why, what and how much questions you should always start with word of mouth references. People who have had an outstanding (or poor) experience with a coach are almost always willing to talk about it.
Courtney suggests VC firms, investors, and connecting with people in the HR field as a few potential starting points. I’d add that you should also talk to peers and people in positions you’d like to grow into to ask them if they’ve benefitted from a coach. Often you’ll find they have!
Courtney also provided a great list of questions to ask after developing your short list of potential coaches—these range from the practical to the stylistic.
There are no right or wrong answers to these questions; there are only the answers that fit with what you want.
The first question Courtney suggests from above relates to the retainer. This is important because there are a wide range of fees that coaches charge.
“I think coaching can range from $50 to $3000 an hour so it's hard to say exactly what to expect from a rates perspective. I have heard that Tony Robbins charges a million dollars retainer for each of his clients (!!). Generally a lot of the coaches I know who are experienced charge between $300 and $1000 an hour.”
How you structure it with your coach is equally important. Some coaches will ask for a certain level of commitment. This is why the “how much are you willing to invest” self-inquiry is important. Typical retainers are ~2 meetings per month for 6 months. And at $300 to $1,000 per hour this adds up to a cost of $3,000 to $12,000 per engagement.
This leads us to another question:
Should I ask my company to pay for it?
For my coaching sessions I had the privilege of having companies pay for them and when I went to a new company I negotiated that into my offer package. This is much more common for more senior employees who are often seeing more senior ($$$) coaches. In today’s financial climate—where startups are trimming expenses—this could be one of the first areas that get trimmed (especially for an IC or more junior employee. In that case you may consider a less-experienced coach who brings skills you don’t have (at a cost you can afford), a service like Betterup or a new service called Scale Higher co-founded by my friend Ravi Mehta.
“There are pros and cons to having a company pay for it -- it does happen that when a company is paying for it that sometimes the client takes it less seriously and is less committed (canceling sessions, showing up unprepared, etc). The clients who pay out of pocket are often more committed and the time length of engagement is shorter but I have many very committed clients who don't pay out of pocket. I don't really have an opinion about whether or not a company should pay for it or not. I do think it's an amazing benefit when they will pay for it.”
Regardless of your path there is definitely a coach available at a price point that works for you—just make sure you’re able to address the “why, what, and how much effort” before hiring them because there are also some risks to hiring the wrong coach.
The risks of choosing the wrong coach
I originally asked Natalie and Courtney if the wrong coach could do “damage” and both thought that word was an overblown way of describing the risk. I have a flair for the dramatic so I’ll agree that “damage” isn’t the right way to think about this. Risk is.
Natalie helped me bucket the main types of risk into the following:
Time / Financial. Was your time and money well-spent? Did you get something out of it?)
Social / Reputational. Is your reputation now at stake because you’ve taken the advice of someone that’s led you astray?
Outcome. Did you actually get to your end-goal that you were hoping for?
Opportunity Cost. Was there something else you could have done with this time that would have been more impactful?
These are real risks and so you need to be explicit with your self-inquiry and understanding whether the coaches you’re considering can help you avoid these types of risks vs. steering you into them inadvertently.
Courtney provided a great takeaway on risk and how to escape it:
“I think the risks of hiring the wrong person is that it could be a waste of their time and is not pushing the client to be a more aware and fulfilled person. Time is our most precious resource so if it's not productive or fruitful then it's time to make a change! My biggest piece of advice with coaching is to make sure you are naming when it isn't working and allow your coach to adjust the sessions to better serve them. If it doesn't work after that, find another coach!”
This article is a 🔥Hot Take Alert 🔥 and I stand by my assertion that a young, inexperienced and untrained coach can cause you to learn bad habits and waste time (and money). I also think that the inconsistency in certification and training for coaches, as well as the proliferation of the “advice economy” has led to an explosion in the LinkedIn coaches I vilified above. While I don’t have a solution to that problem I do hope you can use the templates, frameworks, inquiry and interview questions I’ve written about here to find the coach that works best for you.
And that just may be the 25-year old (experienced, thoughtful) coach.
As Natalie puts it:
“Some folks think 25-year olds aren’t mature or experienced enough. Maybe so. I’ve met some really immature 40-year olds, and some really wise 16-year olds. And I think everyone has wisdom and maturity in different realms. I wasn’t really concerned about not having enough experience because I had personally worked with or heard about plennnnnty of leaders who were extremely successful executors, and absolutely terrible coaches. They’re two different skills, and experience in one doesn’t automatically make you skilled in the other.”
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