What Entrepreneurs Should Know Before Hiring a Business Coach [Expert Interview]

When you hit a roadblock on your entrepreneurial journey, it can often feel impossible to push through to the next milestone. 

And it’s a feeling all entrepreneurs face, myself included. While building my previous startup, Venga, hurdles came up, and I was often left feeling lost. 

I wish I’d had a sounding board. An experienced business person who I could’ve talked to about the business issues I was facing. Someone who could’ve helped me push my business to the next milestone. 

I wish I’d known the importance of business coaches for entrepreneurs. 

Having a business coach to go to for advice, almost like a business therapist, would’ve been invaluable for me in the early days of my startup journey.

Someone like serial entrepreneur and business coach Diane Prince.

Business coach for entrepreneurs Diane Prince

She launched her first business in 1996, a recruitment startup, OnStaff. Just six years later the company was making an annual revenue of $50M, at which point they sold the business to a strategic partner (check out the paperwork involved in the acquisition below!)

Acquisiton of Entrepreneur, Diane Prince's company

Since then, Diane has built several companies, across several verticals. Alongside this, she has served as a business coach for many entrepreneurs. 

So, my CMO Rui and I sat down with Diane to talk to her about everything you need to know to be in the best position to find and hire the right business coach for you. 

Interview with Business Coach Diane Prince

Paolo: Diane, thanks for sitting down with myself and Rui. 

Can you start by telling us a bit about yourself?

Diane: I strongly believe in having a deep connection to your “why”. I started my first business with my husband at the time because we wanted to work together. 

It started with a reason that I wanted to personally satisfy. 

I was 26 and working in a cube as an assistant buyer at a computer reseller. I didn’t want to spend my life climbing my way to the top of the corporate ladder. 

The first business I built was an agency. It was very specific and so niche, but we timed it perfectly. The product-market fit was unbelievably good. I started it not knowing anything, neither of us did. 

We got a book on how to build a temp agency for dummies and read it. We heard of other people exploring the niche we were going in to

“I went to step aerobics (it was the 90s) and they were playing that Alanis Morrisette song, Ironic, and I decided there and then, I’ve gotta do this. I quit my job the next day.” 

My coworkers were all telling me how big a risk it was and I said to them: “What are you talking about? I’m 26?” I looked behind them at all these cubes and said “That’s the risk! Sitting in this cube the rest of my life!” 

On the outside, it looked like we were going into a boring business. There were no women or young people in the industry. It was very much not sexy at all. 

But what I found exciting was actually building it. That’s when I realised that building companies was my passion. 

Now I really encourage entrepreneurs to get money quickly. Once you start bringing in money it’s so validating and exciting. And more exciting than that is you have customers! 

In a nutshell, I spent my 20s making millions, my 30s retired, my 40s learning some gnarly lessons and now in my 50s, I’m teaching other people. 

P: What is Business Coaching? 

We hear a lot about advising and mentoring, but maybe you can explain to our community the difference between them and a business coach? 

D: I think business coaching can mean a lot of things. Some business coaches are specifically mindset coaches or performance coaches, etc. There’s a lot of different strategies when it comes to business coaching. 

One thing I’ve realised is a lot of founder business coaches for founders haven’t actually built startups. 

“What I do as a business coach is I combine the mindset part, and help founders get through the many stages of building a business.” 

There’s that first stage where you’re getting everything together; it’s new and exciting. Then there’s the “oh sh*t I actually have a business” stage. And there are all sorts of problems that come with each stage. 

I work with a few founders who are around Series A and beyond. That being said I mostly work with first-time founders who haven’t built a startup yet. 

For me, it’s a combination of the practical things combined with helping to push them through to get to the next stage. Because I personally believe that in a startup you should be focusing on getting from one stage to another – the next milestone.  

As a business coach, I act as their guide in tackling the hurdles all startups face – which can often be overwhelming and demotivate founders. 

“I believe startups fail because the founders have decided to stop solving the problems that naturally arise as you build a company.” 

We hear about startups failing because of cash flow, bad partnerships, bad product etc. And while these are all bad they can all be solved. The only reason to me why things stop is because the founder stops looking for those solutions. 

I don’t believe in telling founders what to do. Instead, I’ll help them talk through the options and what’s coming up for them so that they can make the best decisions for themselves.

For example, one thing that comes up is the question of when a founder should quit their job. I believe that’s different for everybody, so by telling someone what they should do you could be putting them in a challenging financial situation. Conversely, you could be preventing them from becoming the next Mark Zuckerberg. 

“The entrepreneurial journey is so personal. That’s why people start businesses. They want to express themselves in the world and bring their creativity in the form of a business.” 

For me, it’s also the practical part. The things that you do need to do, like cash flow, solid business planning, etc.  

And importantly learning the discipline to carry out the startup process. Once you have that discipline in doing the things you have to do you then have the freedom to be yourself and let your creativity loose.

Business Coaching Session with Diane Prince and two entrepreneurs

The main difference between a business coach and an advisor and a mentor is the relationship you have with them.

With a business coach, you’re paying for their time. You have set times you communicate and set channels to communicate with. Therefore the business coach is committed to helping you complete the goals you’re working towards at that specific time. 

With a mentor or advisor, it’s a different relationship. Specifically, with mentors,  entrepreneurs can often feel guilty that they’re taking up too much of their time – as it’s a volunteer situation. Conversely, mentors are often simply too busy to help out, and there can be a disconnect there. 

Related: Expert Interview: The Ultimate Guide to Startup Advisors 

P: I believe a lot in therapy to help overcome large amounts of stress for example, or to help you learn how to make better decisions.

Would you say that a business coach is a sort of halfway between a therapist and a mentor? A business therapist if you will. 

D: Yeah, I think that’s a really good way to put it. Definitely. 

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Rui: I see what you mean when you talk about the financial relationship. It kind of forces the founder to take action.

Comparatively a mentor shows you the way and it’s up to you to follow it. 

Is there a stage where entrepreneurs are more likely to find a business coach? 

D: I don’t think it’s more prevalent at any stage. It goes back to the comparison Paolo made with therapy. Entrepreneurs hire a business coach when they have a problem, most of the time. 

Sometimes it’s because they see that their performance could be improved, and see the value that way. 

Some entrepreneurs want a business coach from day zero because they simply don’t know where to start. Or they want to talk through how they can handle co-founder relationships. 

But further down the startup road, there are founders who’ve just got funding, and there’s a whole slew of issues. This goes back to the idea of therapy and mentors and advisors. 

You’re not necessarily going to call one of your mentors or advisors to tell them you’re overwhelmed – especially if they’ve invested in the company. 

Whereas if you feel like you want to give up, you can talk to a business coach about that and be vulnerable in that space without worrying about it affecting your stakeholders because it’s confidential. 

Then there are the venture-backed founders, which can be an awful lot of pressure. In that case, a lot of founders will reach out for business coaching in the performance-based mindset. 

P: I read on your website about the importance of having a business coach who has experience in startups – something I 100% agree with – As well as the need to cut bullsh*t out of the relationship. 

In your experience, do you feel there’s a lot of bullsh*t in the startup world? 

D: Yes, one of my taglines is just that, taking the bullsh*t out of entrepreneurship. 

I launched my first startup in 1996, and no one called themselves an entrepreneur back then. You just didn’t say it, you would’ve sounded like an assh*le. 

So I think I really have the advantage of starting up before startups were a big thing. Plus, I had the advantage of going through the big tech boom. 

I had a niche SaaS platform at the time and we hired a consultant who came from Silicon Valley to LA to meet with us. He’s sitting there telling us about how we shouldn’t make a profit on this. We should just go for the biggest market share. And after he left we looked at each other and decided against that, because we had a profitable business. We ended up selling that to one of our employees and he ran it profitably for years. 

There are some businesses where market share is important, and the founders can make money without necessarily turning a profit. But that’s a tiny tiny percentage of startups. 

But this is the kind of BS advice that comes up and it can be really intimidating. And then there’s the VC stage which is a whole other ball game in that respect.

Related: Expert Interview: How to Hire Top Talent in Startups 

P: I found that with Angel Investors. 

I was living in London before and everyone says they’re an Angel Investor there. Even though they don’t know anything about tech or startups, they just have some disposable money and are looking to invest in startups for the fiscal benefits.

I feel like, as a first-time founder, there’s a lot of navigating around what’s real and what’s not.

Now, Diane, I want to move onto actionable tips.

What should an entrepreneur know before trying to find a business coach? 

D:  I think the most important thing is how you connect with that person. Do you know that feeling you get when you’re talking to someone and something feels a little off? Trust your gut in that respect.  

Define who’s right for you depending on your stage or business type and start talking to them. 

I would look for somebody who has built companies. It’s important because if your business coach has been down the path you’re about to go down they’re better equipped to help you through the hurdles. There’s so much value in that. 

Also, you could consider group coaching, which is something I’m delving into now as there’s not much out there for startups at the moment. That may work better for you. 

But take the free calls that most business coaches will offer. 

P: What’s the best way to reach out to a business coach? Is there structured research behind it or is it better to go down the road of referrals and personal connections? 

D: I think looking at testimonials is a really good place to start. 

Sometimes you’re going to find a newer business coach who’ll be really stellar though – but may not have as much experience. 

It’s like anything, ask for referrals, ask other founders who they’ve worked with, etc. But ultimately it goes back to finding someone you really click with. 

P: When a person is looking for a business coach, are there some key traits that they should be looking for? 

D: It’s a combination of things. They should have experience running companies, as we mentioned earlier. But more than that, they need to be able to take that experience and use it to guide someone through their journey. 

So when you’re looking for a business coach you need someone who can relate to you. It has to be someone who can get to the heart of what you’re trying to build. After all, it’s your business, time and money. 

Expert Tip

People, or the ability to ask for peoples’ help, is one of the most valuable resources you have as an entrepreneur. 

Embrace that ability to ask for help, it’s one of the most valuable resources you have. You’ll be surprised how many people will be happy to help. 

Giacomo De Lorenzo, Founder & Entrepreneur

P: And on the other side of the coin, what should a business coach look for when assessing a good entrepreneur? 

D: For me, an ideal client is someone self-motivated and ready to do the work. I want to see people succeed. 

P: Do you focus on a specific vertical at all? 

D: Not at all. I’m interested in helping people build successful companies regardless of vertical. 

But I have a network of advisors and contacts in specific verticals who I’ll bring in to help my clients with their specific industry needs. 

P: I want to talk about the process. I personally don’t have any experience with business coaching, so my question is: 

From the moment I decide that you’re my business coach, what can I expect?

D: Come at it with an open mind, because a good business coach will know what to talk about to help you. I think: 

“If you can be as real as possible when talking to your business coach you can expect a lot of growth.”  

It allows you to take that dedicated time to focus on you and your business. Ultimately it will help you have more clarity and peace and become a better leader and founder. 

P: Obviously you have to tailor-make the experience with each person you work with. 

That being said, is there anything you do recursively with each client, a path you follow? 

D: So, for my one-on-one business coaching it’s a lot more fluid, and less structured. And it completely depends where they’re at. For example, one of my clients has a spreadsheet and we track her activities and her goals, and that’s what works for her. 

Typically, my clients have an hour per week set with me. Aside from that, they have certain times when they can contact me because things happen. Maybe they can’t make payroll tomorrow and they need advice or other emergencies. So I’m available to talk them down from the ledge if you will because there’s always a solution. 

So for one-on-ones, it’s more making sure the client’s needs are met at the stage they’re at personally and professionally. 

For group business coaching, it’s much more structured. 

There are modules and you go through different activities and actions. There’s a product-market fit section for example, and I have the industry-specific advisors with me helping with that. 

P: In the one on one how do you measure improvement? 

D: Again it’s different for each client. One way I’ve measured improvement in the past is with a specific client we used his pricing structure. In that case, he told me he wasn’t a money person, so we improved that process and the results were clear by the end of it. 

One client, in the beginning, was having cash flow issues and collection issues. He was able to step into realising he was the one in control and could set boundaries with his clients. He could ask for money, ask for what he deserved.

We also managed to work out onboarding someone he thought would be too expensive. I helped him realise that by having this player in his deck he could ask for more money from the clients. 

Another one of my clients really wanted to position her business for acquisition. So what we looked at was a way to find someone in her network who was a viable person to takeover. Then we structured an equity agreement with them that made it really exciting. 

So a lot of the time it’s finding those solutions that are right under an entrepreneur’s nose. They’re just so in the weeds and so involved they don’t see the solutions. 

P: Is the approach of a business coach similar to that of a therapist, where you talk and the therapist is giving you the tools to realise what you need to do.

Or is the job of a business coach to provide the solution for an entrepreneur?

D: I think it’s both. Overall it’s about helping them gain the tools for themselves, as we’ve discussed. 

That being said, sometimes in business, you need a solution quickly. And as a business coach, I think if you can give them that solution, where appropriate, you should. 

P: Let’s say you have a relationship with someone, when do you consider it successful? When the problem they came to you with is solved? 

D: It can be a myriad of different things. One obvious one is you see tangible results. Other times it’s that they’ve gained peace of mind. I generally work with the CEO or main founder of companies. Some of whom won’t tell their co-founders they’re working with me. One of my clients, for example, has said that I’m her secret weapon. I love that. 

For her, like a few of my clients, it’s about having a sounding board. So before they go into big co-founder meetings we’ll talk things through and often sit down again afterwards to deconstruct it. They find that valuable. 

P: From the perspective of a business coach, how can you tell when the relationship isn’t working?

D: When someone’s not ready to implement the tools I can give them. And it happens, sometimes change is hard. 

I haven’t experienced it personally yet, thankfully. 

P: I wanted to move on to some practical questions. 

Firstly, what’s the typical duration of a business coach-founder relationship?

D: It completely depends from person to person. Some people want to continue that relationship after their main problem is solved to have that sounding board as I mentioned, others don’t. 

For example, having a business coach as a solo founder, or as someone looking for a co-founder can be very beneficial. A business coach can be a very good person to bounce ideas off when you don’t have that co-founder yet. Which means you won’t feel the need to rush into that business marriage. 

Also, as a founder, if you have a team without a co-founder it saves you from talking to your employees about core ideas or issues in the business.  

For example, sometimes if you’re sharing ideas with your team they’ll start implementing it when it’s not the right time. I’ve personally had that issue before and they want to make you happy. 

P: What’s the typical cost of a good business coach? 

D: It’s such a big range. A business coach can set you back anywhere between $250 an hour to $5,000 a day. It depends as well on the complexity of the problems and what steps are needed to solve it. 

P: Finally, Is there any advice for entrepreneurs reading this who may feel a little lost in the Silicon Valley bullsh*t? 

D: I think just to get out there and try it. And, when it comes to business coaching, invest in yourself.  I have my own business coaches and one of them is insanely expensive. When I found out how much she charged I thought “She’s crazy!” But then after one session, I ended up hiring her because her advice was worth the money for me.

“I’ve made million-dollar mistakes and I think business coaching is a way to avoid making those mistakes, so it’s worth the investment.”

P: Diane, thank you so much for your time, where can readers learn more about you and the programs you offer? 

D: To learn more about how I can personally help you and your startup, check out my website or connect with me on LinkedIn.

Wrapping Up

From a sounding board to someone who can help you achieve specific business goals, business coaches can help you reduce your risk of failure.

Just ensure that you onboard a business coach who is right for your specific needs.

Below are some FAQs that summarise some of the things we discussed with Diane. 

Thanks for reading.

FAQs Around the Topics Explored in This Interview 

What Is a Business Coach? 

A Business Coach is an experienced professional who helps guide your entrepreneurial journey. 

A business coach is there to help you: 

  • Develop your entrepreneurial mindset
  • Navigate the various stages every business faces 
  • Talk through problems and pain points you may be facing  

How Much Does the Average Business Coach Cost? 

An average business coach can cost anywhere between $150-$350 per hour. That being said there is no minimum or maximum price when it comes to business coaching. 

 It’s important to note that you should be focused on finding a business coach with experience in entrepreneurship and startups. And more expensive doesn’t necessarily mean better. 

What Should You Expect From a Business Coach? 

A business coach should help you: 

  • Define your vision for the desired outcome – e.g. increased sales, increased visibility, more customers, etc. 
  • Provide an objective and transparent view of your current situation based on their experience – both the internal and external factors impacting you and your startup. 
  • Guide you to implement processes to move your startup to its next milestone.