How To Get Incredible Value From A Coaching Session

Every now and then, you find yourself in a conversation that changes your career.
It might be random encounter that leads to a new client or new job.
It might be some frank feedback, with the power to inspire you or scare you.
It might be a mentor or advisor suggesting you investigate an opportunity you’ve never heard of.
It might identify a blind spot, or encourage you to double down on your strengths.

While these can happen by chance, you can also engineer them.
If you talk to smart people, with the right questions and the right expectations, you can massively increase your odds of having a career-changing insight.
That said, I see a lot of people miss these golden opportunities.
They avoid these conversations, deliberately or accidentally, and end up needlessly limiting themselves.
I’m lucky enough to have the support of several incredible coaches, as well as a large number of coaching clients.
The following tips will boost your chances of gleaning invaluable advice in a short space of time, and maybe even help you coach others in the future…

Identify what this person can do for you
Before talking to a new coach, it’s worth asking yourself how this person might bring a new and valuable perspective to your situation.
Maybe they know more than you.
Maybe they bring fresh eyes and raw honesty.
Maybe they’ve done what you’re hoping to do, even in another field.
Maybe they can introduce you to the right book or resource.
Maybe they can introduce you to the right person or company.
Maybe they can be a great source of accountability.

As Matt Mullenweg said:
“Everyone is interesting. If you’re ever bored in a conversation, the problem’s with you, not the other person.”

Decide to be 100% honest
What’s the point of telling your coach or yourself little lies?
I get why people do it in casual conversations, but why lie to the person who can potentially help you?
For example, I found that by being honest about my emotions, hesitations, insecurities and progress, my coach can help me see which of them are genuine issues and which of them I’m overthinking.
In fact, just being honest with myself brings 60% of the benefit.
If you don’t think you can be honest with the person you’re talking to, that’s ok, but you need to also find another coach.

Make a list of what you’ve been thinking about
“Plans are useless, but planning is everything.” – Dwight D Eisenhower.
Before I meet with an advisor, I find it helpful to make a list of what’s on my mind, even if we only end up discussing 2 or 3 of the topics.
Vice versa, it’s helpful for me when my clients write out some thoughts in advance, some of which are quick wins, some are not things I can help with, and some are deep discussions.
Either way, this helps us quickly identify the most valuable points of conversation.

Run towards the discomfort
Some of the topics on your list might make you feel uneasy – that twinge in your stomach is telling you that this isn’t just a head-level conversation.
You have three options:
·      Try to bury the topic altogether
·      Subtly dance around the topic
·      Proactively bring it up

My suggestion is to go with option 3, but I find a lot of my clients start with option 2.
That gut feeling is a sign that you want to bring it up, so that you can get it out of the way.

Separate out the technical problems from the adaptive challenges
A neat trick for breaking down problems is to ask yourself “is this a technical problem, or an adaptive challenge?”.
Technical problems require technical solutions, like the need to buy a piece of equipment, obtain a licence, fix an issue with your website or learning how to run an Instagram ad.
Adaptive challenges require new beliefs and behaviours, like the decision to publicise your brand, to change your management style, or to reverse your position on a previously controversial idea.
Each of these can be overcome, once you name them correctly.
You can’t change your mind out of a technical problem, and you can’t buy your way out of an adaptive challenge.
Your coach can help, by asking good questions that clarify what category each issue falls in to, and then processing your options for reaching a great resolution.

Create a little action plan
A great way to wrap up a coaching conversation is to pick the three things you’re going to do next.
Action plans are useful because they force you to be clear on what needs to happen, and if you don’t know what needs to happen then it’s a clue that you need to ask more questions.
There is some weird magic in the number three – I find that declaring more steps generally increases the chances that nothing will actually get done in the next few weeks.
Ideally you want three next steps that you can begin to implement straight away, like reaching out to someone via email or phone, creating a single piece of content, or writing a proposal for a new idea.

Read related books
When a topic comes up that you don’t know much about, you can get a tremendous amount of value from reading one or two books on that topic.
Books aren’t that expensive, maybe $15-20 to get thousands of dollars’ worth of immediate reward.
For example, one mentor told me that their favourite book was The Four Disciplines of Execution, so I bought it that afternoon.
They were spot on – for $15 I now had a huge collection of extremely relevant advice.
The same goes for my clients, I end up recommending books like The E-Myth Revisited or To Sell Is Human, and the people who actually read the books always comment the next time about how useful it had been for their business.
Good coaching isn’t cheap, but an extra $20 on the right book can double or triple the benefits from your session.

Put your hand up when you get stuck
It’s hard to know what to make of a prolonged silence.
On one hand, things might be going really well, but in a lot of cases a long silence means that someone is stuck in a rut.
Rather than pretend that the rut will magically end on its own, why not use your one bit of proactive energy for the day to flag it with your coach.
The act of naming the rut is surprisingly helpful, and a single text or WhatsApp message can restart your momentum.

Celebrate all your wins
Most of us feel the losses when they happen – it’s hard not to.
Wins on the other hand, we sometimes need to deliberately enjoy.
Wins aren’t just the final celebrations either, they’re the milestones along the way.
e.g. your first customer, launching a new product, hitting $30k in monthly revenue, raising your prices, securing a partnership, hiring your first employee, rebranding, overcoming a fear, speaking at an event, hitting your growth targets faster than expected, etc.
You and your coach might not be best friends, but they are uniquely positioned to understand the significance of these achievements.

Deliberately keep up your momentum
Enthusiasm is generally at its highest immediately after a session.
That enthusiasm tends to fade, so to make the most of your new decisions, you’re going to want to take a second step within the first 72 hours.
For me, it might be ordering a book, signing up to a platform, arranging some meetings, setting out the next ten steps, breaking things down into 1-2 hour tasks.
If I can’t break things down into 1-2 hour tasks, I don’t understand my project well enough, and need to ask more questions.
In other words, I get enthusiastic me to make commitments for future me, before life gets busier and I get distracted.

If you don’t have a coach, I highly recommend reaching out to someone who can save you time and help you earn more money.
They might be a professional coach, or a knowledgeable person in your field.
It can be for a season, it doesn’t have to involve a long or expensive commitment, but it is different to just catching up with a friend.
If there is a coach that can improve your work and mindset, surely they’re worth seeking out?