Many small business owners find out the answer to that question the hard way - through making mistakes, dropping a ball or some similarly uncomfortable experience that highlights a gap in their knowledge.
Such 'learning experiences', though, can be the prompt for business owners to seek out further education - whether it's through relatively formal channels like enrolling in courses, or less formal opportunities such as reading blogs, business books or reaching out to networks.
This week I've spoken to a number of small business owners about some of the things they've done to further educate or upskill themselves as business owners, and the impact those experiences have had on them personally, as well as their operations.
Craig McFadyen is a founder, along with business partner Derek Good, of online business training company LearningPlanet. The pair are experienced business owners, having developed other companies including a traditional business training firm, Rapid Results, which they recently sold. However, they decided to enrol in Massey University's Sprint Programme, which helps entrepreneurs validate and develop their business ideas, given LearningPlanet was taking the pair into relatively unknown territory.
"It definitely clarified some things we needed to know," says McFadyen. "It's one thing running your homegrown business that's dealing with local people, but it's another to be going into a technology business that you want to take global. You need completely different skillsets and there are different pitfalls you can fall into."
Daniel Sadler bought the Newmarket branch of Office Products Depot (OPD) three-and-a-half years ago, and is now also a director of Silver Fern OPD. He spent the first year-and-a-half in his new business getting his head around how things worked - a process that he says also highlighted "some real gaps in my understanding of how to run a business - things like how to manage people and resources, and time management".
So Sadler signed himself up for the Owner Manager's Toolkit course run by the Employers and Manufacturers Association, which involved attending three-hour classes once a week over the course of three months covering a broad range of business owner 'need to knows'.
Sadler says the course gave him the confidence to make some "hard, strategic decisions" and he's implemented many of the ideas he learnt. In terms of tangible business results, he cites sales growth at the company last year of 9.5 per cent, compared with previously flat growth.
One challenge many of the business owners talked about was finding time in their schedules for taking on learning opportunities.
Emma Thompson - an aspiring company director and the managing director of Nelson-based public relations consultancy Etc Communications - now sets aside one day a week for non-client related work, including learning opportunities.
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"Generally, I think learning while working can be difficult when you have a small business, and it can get postponed to 'next week'. The trick for me is to not let the learning distract from meeting work deadlines," Thompson says.
Thompson took a week out in Arrowtown to complete the Institute of Directors' Company Director's course to further her governance knowledge, and says planning to do the course eight months in advance also meant she and her team were well prepared for her absence when the time came.
As well as attending traditional courses, many of the business owners talked about embracing more informal learning opportunities.
Like Sadler, Kim Voon - the founder of Auckland-based online marketing agency Insight Online - completed the EMA's Owner Manager's Toolkit course. He's also had a business mentor, has completed sales courses, networks with a range of groups and is a "fanatical reader".
"I also have people that I look up to, and I try to keep up to date with them on Twitter and follow their blogs. I'm a huge fan of Wil Reynolds, Rand Fishkin and Ian Lurie, who run really successful online marketing companies in the US, and closer to home I'm a big fan of Rod Drury."
Craig McFadyen, LearningPlanet
Craig McFadyen and Derek Good are the founders of online business training company LearningPlanet - an idea they validated and developed as part of Massey University's Sprint Programme. After recently selling their traditional business training company, Rapid Results, the pair are now based at Massey's ecentre business incubator, where they are working full time on LearningPlanet.
Your background is in setting up companies to train people working in business, but what's been your own journey in terms of educating yourself as a business owner?
It started 25-plus years ago back in England when I first moved into office-based sales roles. In those early days your induction programme for those kinds of jobs was 'here's your desk, here's the phone, there you go'.
As it happened the job just clicked with me and because I was really good at it, a lot of people would come to me and say 'can you show me how to do that?' That proved to me there was a gap in organisations to train people for those kinds of skills.
We moved to New Zealand during the recession in the early nineties and back then we didn't really have call centres in New Zealand. Because I had that experience, I got a job in a few weeks setting up and running a contact centre here and then about 18 months later got headhunted by Ernst and Young to head up their contact centre consulting division. That lasted about two years until someone said to me 'why aren't you doing this for yourself?'.
So I walked out of my job on a Friday, and on the following Monday I started my own business. I thought 'now what do I do?' I had no business training, so I picked up the phone and rang everyone I knew to look around for business mentors and coaches.
And I would go to every workshop or conference I could find, read every book. That became my whole philosophy: surround yourself with people who know the stuff you don't so you always have people to bounce ideas off who can help fill those gaps.
How did you get around the perennial startup owner challenge of being time poor?
I think you just have to accept that it's what you need to do. The fact with any startup business is there's so much to learn and it's not until you get into it and you start making mistakes or things don't get done that you see how much you don't know.
Most of the time businesses are set up by technicians - people who are really good at what they do - who often don't invest enough in themselves to learn about the business side.
It comes down to a decision: do you want to build a company with staff and grow it to the point where it potentially runs itself, or do you want to buy yourself a job? If you decide the former, then you need to realise you have some knowledge gaps and then go about filling them. That's where I think the incubators can really help.
How did joining an incubator programme like Sprint help you?
Firstly, it helped us learn if we had a business, by going through the whole validation process. We were already quite well down the track with LearningPlanet before we got approached about the Sprint Programme, and we were a bit different in that we'd already run multiple businesses before. But it definitely clarified some things we needed to know.
It's one thing running your homegrown business that's dealing with local people, but it's another to be going into a technology business that you want to take global. You need completely different skillsets and there are different pitfalls you can fall into.
So, for example, for 20-odd years we'd written a faithful business plan each year then put it in a drawer and didn't think about it again for another year. Then we came here and they threw that model out the window. Now we have a one page business 'canvas' and we use post-it notes on it, which is so much more relevant and saves so much time.
Another benefit was the incubator's ability to put us in touch with and surround ourselves with the people we need, but who you wouldn't normally have access to - or even know where to begin to find them.
Two years down the track, when we sold our other business and started focusing on LearningPlanet full time, we jumped at the chance to take some office space here because of that. Even now they've helped us put together an external board of advisors with some brilliant business minds that we'd normally have no idea how to get hold of.
What other opportunities are you taking to further upskill or educate yourself now?
Being in the incubator, it's just about having the opportunity to tap into the knowledge that's here when you need it. For example, we've never built an online global product, so being able to tap into some of the technical expertise of the people here and being able to sit down with them and have those conversations is great.
It's knowing you have those people behind you when you need them. On the other side, one of the things we want to do when we've made it with this business is give back to that network and share some of the learnings around our success. I'd really like to be in a position to do that in a few years.
Lastly, what's one key learning from your own education in business that you'd like to share with others?
Be the best you can, because if you don't want to be the best, why bother?