Coaching: why you should learn how to do it and why you need a coach too

We’ve all seen this advice: don’t tell your people what to do; instead, set the context for them, define goals with them that they’ll find challenging and exciting, and help unblock things along the way. And yet, when my reports would ask me how they should solve a particular challenge, I’ve certainly found myself telling them how to do it, or, on my better days, how I’ve solved similar problems. I wasn’t following the well-meaning advice not because I thought I was smart and my reports weren’t, and not even because it was way faster to just tell them how to do it vs. having them figure it out on their own. I just didn’t know how to do it differently.

Enter coaching. I’m not close to having mastered it, but in the last year or so I’ve gotten a strong sense of what good coaching looks like, have personally experienced the benefits of effective coaching, and have seen how transformational coaching can be when leading people.

Why everyone needs a coach

  1. You know when you get together with close friends and one friend shares their current struggle in a relationship? And what to do next is 100% clear for everyone but them? It’s much harder to see the path forward when you’re burdened by all the details of the situation, and you’ve thought about it for like 40 hours, and you’re emotionally attached to it. That’s why it really helps to have a third party – your friends in this example, or a coach in the professional setting – to guide you through it.
  2. There’s a reason elite athletes have coaches. If Serena Williams needs a coach in her craft, so do you.

If getting a coach sounds daunting and expensive, read on for tips and tricks. And: help someone else out by being a coach to them!

What coaching is and why it’s f&*$%ing amazing

According to Coaching for Performance, “coaching is unlocking people’s potential to maximize their own performance. It is helping them to learn rather than teaching them.” Coaching is not dependent on a more experienced person passing down their knowledge. Coaching is about partnership, collaboration, and believing in potential. Coaching is a conversation between equals.

See here for concrete examples of questions. A few fascinating things about these questions:

  • They are open-ended and don’t require any prior knowledge or subject matter expertise. One of my personal mental blocks has been “What value can I add to managers reporting to me who are more senior than I am?” I know this is a standard concern for managers of managers. Coaching provides one strong answer to this. Coaching doesn’t require you to be more experienced than the person you’re coaching. The whole basis of coaching is that the coachee already has the answer in them – you’re just helping them get to it!
  • For everyone trying to be more mindful, coaching is a great exercise in being present. It’s about working with what the person you’re with is saying vs. bringing in your knowledge/experience/ideas. When you really commit to it, it forces you to listen to your counterpart actively – as opposed to listening to the voice in your head that’s collecting argumentation for the brilliant point you’re going to make when the other person stops to take a breath.
  • Coaching is also an exercise in humbleness. When in coaching mode, you aren’t supposed to mention how amazingly well you’ve solved this problem before, or even how you’ve screwed it up and what you learned from it. The coaching conversation is emphatically not about the coach (hard to swallow!) but about the person receiving the coaching.
  • An obvious benefit of coaching is that the coachee discovers and authors answers on their own, Inception-style, and these revealed truths stick much better than some smart thing you share.
  • Compared to mentoring and directing/teaching (see below), coaching develops the coachee’s meta-skills of figuring things out on their own and dealing with mental blocks. It’s theoretically possible to coach oneself (although if you succeed at it, tell me how please 🤔) – you’re helping your coachee develop the requisite skills to do so.
  • When done right, coaching creates a space of respect, support and trust in the coaching pair. This is an obviously good thing for you to have with your reports.

Contrast coaching with mentoring and directing/teaching, which aren’t bad things in themselves and certainly have a prominent place in a manager/report relationship.

The word “mentoring” originates from Greek mythology. Odysseus, when setting out for Troy, entrusted his house and the education of his son Telemachus to his friend, Mentor. “Tell him all you know,” Odysseus allegedly said. Mentoring is about sharing your experiences for the benefit of your conversation partner.

Mentoring can be effective when guiding someone to not reinvent the wheel. It can be faster for solutions that are well-understood and the coachee is likely to accept.

I know I personally overdo mentoring. It feels less obviously annoying than telling people what to do and more accessible/natural than coaching, plus I love talking about myself, so I default to “well, what has worked in a similar situation before…” After I learned about coaching and thus theoretically removed the knowledge barrier to doing it, not slipping into mentoring became my main challenge.

Directing (a.k.a. teaching) is telling another person what to do. Directing is obviously a great approach to take when onboarding someone to a new problem or role. That’s not the place to have them look inside their soul for the answer – just give them the context and how it’s currently done so they don’t have to guess, being careful to indicate that new ideas are encouraged. Directing can also come in very handy in a crisis situation when getting everybody focused and productive solving the problem in the minimum time possible is more important than deep buy-in, self-discovered logic, and meta-skill building.

As a manager, especially in day-to-day problem-solving, you’ll find yourself incorporating all three approaches into conversations with your teammates. That’s natural and great. Just be aware of what mode you’re in and experiment with your non-default modes!

How you can start coaching

Realize: anyone can be a coach to anyone (if the coachee wants it of course). Peers can coach peers, reports can coach managers and managers can coach reports. When starting to incorporate coaching into your interactions, having as little context about the problem as possible is actually helpful, so you’ll be less tempted to present your solutions or your past experiences.

Coaching doesn’t have to be a big lift: incorporating a few coaching questions into an otherwise mentoring/directing conversation can be a great start. Don’t let striving for perfect prevent you from starting in the first place!

Print out the list of coaching questions and stare at it between meetings. The list is kind of long and can be overwhelming, so pick a few questions that you particularly enjoy. Pepper them into your interactions. The funny thing about them is you often can repeat the same question a number of times to get the person to really think things through, so you don’t need to worry about memorizing all 56 of them.

If you’re an insecure overachiever like me and want to read up on some serious literature, get a book or two on coaching. I recommend this one.

I highly recommend getting more exposure to good coaching. Get a coach that is clearly on the next level and learn by experiencing being coached. This will show you what good looks like. This has worked extremely well for me and has materially sped up my understanding of and adoption of coaching. A lot of companies these days will sponsor a coach for executives and potentially managers. If that’s not an option, explore paying your own money for coaching. Given that 1:1 sessions can be pretty expensive, look into group coaching, which is a thing. If these options aren’t available, ask a colleague you respect to coach you; maybe you can even practice by coaching each other? 🤯


How have you incorporated coaching into your work life? What’s worked and what hasn’t? Share in comments below!

Leave a Reply

Close Menu