How to Effectively Coach a Small & Medium-sized Business

small business coach
March 15, 2023
Table of Contents

The recent years have been good for small business coaches; the startup business is in big boom. 

If all goes well, a startup can graduate to becoming a larger company either by opening another office, generating revenues greater than $20 million, having more than 80 employees, or by getting acquired – as per Forbes.  

While that is the dream of all startups, the harsh reality is that they’re rather vulnerable to risks. According to statistics, 90% of startups around the globe fail. In fact, 2 out of 10 business fail in the first year of operations itself. And on an average, it takes 2-3 years for a startup to make profit. 

These numbers tell us that running a successful startup or a small business is no piece of cake. And that those few who do get to taste success, must be doing something that is working for them. 

And one of those things, for many small or medium-sized business owners, seems to be coaching. And that shouldn’t be surprising because numerous studies have found coaching to have positive effects, such as increased goal attainment, resilience, retention, engagement, motivation, workplace well-being and overall improved performance. 

According to Ram Gopalan, an Executive Coach of 10+ years and the Co-founder of Simply.Coach, the level of motivation he finds in startup founders and entrepreneurs in general has been much higher than others – an employee in a company, for instance. He also finds that they often have much more clarity in terms of what they want to achieve.  

Here are a few things he suggests for a business coach for small businesses: 

1. Work with milestones 

Instead of trying to set goals, set milestones. Usually, with founders, the goals are more or less around the following lines: run a successful business, see business grow, scale, make profit, become an industry leader, and the works….  

So, instead of working on these generic sorts of goals, work with short milestones instead. Doing this helps them walk on the path towards that larger objective and see it more clearly. As a startup coach, you can help them ascertain the pace at which they wish to go and establish what some interim milestones on the path to success would look like. 

2. Pay attention to the emotions  

Amidst the business’ growth, the emotions of a business owner also need to be paid attention to. The startup journey is nothing short of a roller coaster ride – there’s a lot going on: setting up the company from scratch, fundraising, dealing with customers, business growth, scaling, marketing, sales…. In the midst of all this, a small business coach can help the founder manage themselves and their emotions. This is a crucial aspect in the coach-client relationship. 

3. Help them establish structure 

Unlike a well-established company, a startup is not so structured. Things are usually happening in a very haphazard manner; circumstances are changing very quickly. 

A coach can, in such circumstances, help the founder step back, reflect, and connect it all back to the bigger picture, connect it back to what they are learning, and thus, what they can do better. They can help bring more structure where it’s missing and help the entrepreneurs recognise skillsets that they are going to need for what they want to achieve.  

4. Help them prioritize 

In a small business, there is usually very little maturity in terms of organisational functions such as marketing, customer support, sales, etc. And in such a setup, the entrepreneur is very often multitasking and performing several roles at once. In doing so, they often get constrained in their own thinking and end up ignoring matters at their own peril.  

In such circumstances, a small business coach can help founders prioritise things – to help them see and understand which battles are worth picking up and which can be let go. 

5. Stick to your role 

An important point to note is that coaches should be wary of becoming mentors or advisors or consultants to the client. As a startup coach, you should help the founders find their own answers, and not simply hand it to them. By doing the latter, you also end up taking their entrepreneurial power away from them. 

Lastly, a nuance one needs to be cognizant of is that most coaches may not be successful founders or entrepreneurs themselves. Typically coaches comes from a corporate background or they might have been part of businesses, but not necessarily as founders. So, a coach runs the risk of judging the founder they are coaching, thinking their goals or ambitions are too lofty or perhaps not enough. 

However, you must never limit your client. You don’t need to encourage them either. It is very important to understand the role that small business coaches play – there’s no need to put the brakes for the client, nor is there a need to encourage them to shoot higher than they currently are. It’s their call to take – and coaches need to be careful not to bring in judgments, prejudices, or personal opinions. 


1. How do you coach a small business? 

You would coach a small business just like you would coach any other client! Every client has specific needs that are unique to their situation and the same principles of coaching would apply when you are having a conversation with them. You can further enhance the journey by bringing in coaching tools that are relevant to the stage of business your client is at, such as a SWOT Analysis, Delegation Tool, Budgeting Tool, Project Management & Tracking, and more. 

2. What skills should a small business coach have? 

Any coach should ideally have good communication skills, be a good listener, and be supportive towards their clients. Having relevant experience in a similar domain as that of the client is going to be a huge asset – not necessarily to bring in expertise (unless that’s specifically been requested for), but to be able to bring in an understanding that any other coach may not be able to provide. 

About Simply.Coach

Simply.Coach is an enterprise-grade coaching software designed to be used by individual coaches and coaching businesses. Trusted by ICF and EMCC-credentialed coaches worldwide, Simply.Coach is on a mission to elevate the experience and process of coaching with technology-led tools and solutions.  

About the author
Content Marketing Manager @ Simply.Coach

Ipsita Nayak is a full-time writer-editor-content strategist and a part-time NLP coach and yoga teacher. She believes conventions are overrated, has a disproportionate need for solo time over social time, and loves a good mix of sci-fi and trashy TV in her free time!

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