Why I Hired a Business Coach
Plus, things to know when considering hiring one yourself.
It’s easy to picture the titans of the corporate world as lone wolves.
Armed with fearsome intellects, razor-sharp intuition and foresight, alone on the frontiers of what’s possible in the realms of business, technology, and innovation.
Figures like Elon Musk, Steve Jobs, Mark Zuckerberg — they’re all portrayed as solitary geniuses, presiding over their tech empires with near-omniscience. You wouldn’t be alone in thinking their success was the result of a one-man show.
But that fantastical image couldn’t be further from the truth.
The reality is that behind all hyper-successful individuals exists a network of people willing to lend support, assistance, and guidance at critical times. This can take many forms; a co-founder, a supportive partner, a mentor, an investor.
Then there are those whose objectives are far more specific, someone who’s getting paid to guide you to success: a business coach.
The most famous business coach of all time is probably Bill Campbell. He coached Steve Jobs, Sheryl Sandburg, Ben Horowitz, the Google co-founders, and many others in Silicon Valley, and is the subject of the book, Trillion Dollar Coach, released in April 2019.
Deciding whether to hire a business coach is a tough call. And so it should be. It’s expensive, and a time commitment for both you and your potential coach.
But a successful matchup could have resounding effects on the success of your company, especially if you find yourself at a standstill, not quite sure what to do next.
I’m going to tell you about why I decided to enlist the services of a business coach. I’ll share how I knew it was the right time to do so, the difference it’s made to Proposify, and what that coaching looks like from a day-to-day perspective.
More importantly, I’ll explain how you can go about finding a business coach yourself.
Why I decided to hire a business coach
It was early 2017 when I started to plateau.
We’d found product-market fit with a functional product and were hitting solid growth numbers.
Proposify was at the point where it was bigger than any company I’d started before. We had a solid, recently-instated leadership team in place. I was no longer the startup entrepreneur trying to wear lots of different hats all of the time.
I’d reached a point where I didn’t really know how best to manage my time and lead effectively as CEO and co-founder.
So, I reached out to Dan Martell.
Prior to that, I’d heard about Dan a fair bit. He’s very well connected in the startup world and I’d heard him talk at a conference back in 2014 and really got a lot out of it.
I first met him at another conference in Toronto a few years later and invited him to come on my podcast. He was just starting up his coaching so after I told him I was interested he invited me and some of the Proposify leadership team to a full day of coaching at his house.
We came out of that session thoroughly impressed. Dan shared a lot of leadership tactics and principles, some of which are still in place at Proposify today.
After that came an offer to join the SaaS Academy, a community of founders looking to scale their product and grow revenue. It was a perfect fit.
A day-to-day look at my coaching as it currently stands
Just this year, I got a call from Dan asking me to get in on his exclusive one-on-one coaching group JFDI.
(JFDI stands for Just Fucking Do It, in case you were wondering.)
This is an even more niche program for SaaS founders. There are only about seven entrepreneurs in the program, each in the $5–10M ARR range. I was certainly in impressive company. It’s inspiring to rub shoulders with them at our events and group calls.
Each month, Dan hops on individually with each member of the group and checks in on what he calls the five dials. Each dial represents a specific goal of the founder and provides a metric to track. They are:
- How many leads?
- What’s the cash flow?
- How many free days?
- How many genius days?*
- How much profit is in the company?
*A genius day is a day spent on things you’re passionate about, things that ultimately let you as a founder keep your sanity and therefore add more value to the company.
Each quarter, I design a project and a goal for where I want to be with each dial for the next quarter. When we meet one-on-one, we review each dial and see if I’m on track to hitting my goals.
Possibly the most value of the JFDI program lies in the events. Where the SaaS Academy events are larger-scale presentations, these are intimate boardroom sit-downs with other JFDIers. Dan frequently sets up site visits with founders, sometimes from billion-dollar SaaS companies, where the group gets to meet that CEO and discuss how they got to where they are.
So, this is just a little snapshot of the coaching I’m getting. Every coach takes a different approach depending on their clients, the specific goals they have, and the industry in which they operate.
The results: priceless advice on scaling up
I sought out business coaching at a pivotal point in Proposify’s life.
We just assembled a leadership team, but for many of us, it was the first time we found ourselves in management positions. We didn’t have a lot of structure in the company.
As the CEO, I knew how critical it was to design and implement a structure that would serve as the foundation that supported the kind of growth I knew we were capable of.
I couldn’t afford to get it wrong. Even the most efficient framework is no good if it can’t handle the weight of scaling.
Coaching helped me figure out the systems and processes I needed to put in place to grow — it provided that crucial structure.
Dan acquainted us to the Entrepreneurial Operating System, or EOS — a framework outlined in the book Traction by Gino Wickman — as a way to structure departments, communicate more effectively, and delegate tasks among the company.
As we’ve scaled as a company, that system is still in place. It allows us to track progress and develop a regular cadence of communication through the leadership team and down into each department.
In 2018, Proposify scaled from 20 employees to over 60 and we are continuing to grow. If it wasn’t for the strength of the foundational framework and systems, we may well have crumbled under our own weight. Guidance on how best to design a robust framework that can handle rapid growth is one of the biggest things I’ve gotten out of business coaching.
Deciding if and when business coaching is right for you
So I’ve outlined the reasons why I hired a business coach, and what that coaching has looked like since, but how do you decide if coaching is right for you?
Whether it’s to get out of a rut, to get some guidance when you’re feeling overwhelmed, or to level-up your skills as a founder, there are many different reasons to hire a business coach.
As I’ve said already, bringing on a legit coach is not a decision to be made lightly. Coaching is expensive, a serious time commitment, and the beginning of a relationship that goes beyond mentorship.
A mentor is a valuable asset, especially for someone just starting out, but the dynamic is fundamentally different from a coach. A business coach is getting paid to help you.
It’s a close relationship, and it won’t really work if it’s not. There shouldn’t be any secrets in your business that your coach doesn’t know about.
Unlike an investor, or a partner, or a board member — someone with skin in the game — a business coach isn’t financially connected to the success or failure of your business beyond the fact that he’d likely lose you as a client if things go sideways.
Whereas you need to be very careful about how you communicate with an investor, you can be blunt with your coach. Their job is to help you succeed, and they need to know exactly what they’re up against to do so.
Hire a business coach who’s been in your shoes
Do you think Coach Carter would have had the same success had he coached a lacrosse team? What if Patches O’Houlihan coached a chess team instead of dodgeball? (“If you can dodge a wrench, you can dodge a rook” just doesn’t have the same ring.)
Likely not.
So why would you hire a coach from the manufacturing space for your B2B SaaS company?
The best coaches know the game better than the players. In business, it’s crucial they understand the industry you operate within; they get the lingo and know the pain points and the strategies which lead to success.
For me, I needed someone who knew the subscription model back-to-front, knew strategies to reduce churn and increase lifetime value, bump up average revenue per account, how to best market a SaaS product, which metrics to apply to track the effectiveness of the sales team…
You get the idea.
I needed a coach with super-specific industry knowledge. Someone who can speak to the challenges I’m facing because he’s seen them before.
That’s why Dan’s coaching has been so valuable to me. He’s built SaaS businesses before. He’s got first-hand knowledge and knows how to disseminate relevant, actionable advice. A coach guides the choices you make and holds you accountable for following through on those decisions.
Sometimes, business coaching goes beyond industry strategizing and corporate guidance. A big part of Dan’s coaching revolves around the health and wellbeing of his clients. For instance, he has a nutritionist who keeps me accountable for my diet, how much exercise I’m getting, water intake, and the kind of sleep I get.
Finally, you need to like your coach, and they need to like you. Coaching is a big commitment. You both need to get along for that relationship to bear fruit. Both of you should be able to walk away at any point if things don’t go as planned.
So, should you hire a business coach?
Business coaches can get a bad wrap. Bad ones do little more than dish out the same cliches you’d find on a bumper sticker or ‘inspiration’ posts on Instagram.
But great coaches can change the course of your business for the better. Great coaches are committed to helping you achieve your goals, whatever they might be.
If you’re thinking it might be a good time to hire a business coach, I can’t stress enough the importance of doing your due diligence.
Find someone who speaks your language, helps you formulate measurable, specific goals, and is genuinely committed to helping you level up and scale your business.
Enjoyed this article? I’d appreciate you giving it some claps. Also if you’re an entrepreneur, check out my book, Free Trials (& Tribulations): How To Build A Business While Getting Punched In The Mouth available on Amazon
