11 Great Coaching Questions for New Scaleups

Neil Lewis
5 min readOct 7, 2019


Are you ready to scaleup your startup?

Here I’m sharing 11 great coaching questions that our clients have used to transition from the startup to the scaleup phase and speed up and smooth-out scaleup growth.

Okay, so what exactly is a scaleup, I hear you ask!

Traditionally, a scaleup is identified by speed of growth, in sales, user capture, revenues or investment.

However, in coaching, we don’t find that a very useful gauge as it ignores many excellent — high growth — businesses that are moving to their next phase but missing the expected ‘growth’ numbers for one reason or another.

Instead, to identify when startups are beginning to scale, and can benefit from Scaleup coaching, we look at how the focus of experimentation shifts.

In the startup stage the experimentation is focused on the product / service and how it fits a particular market. So, we have questions such as: will people buy/ use this product / service? How much will people pay? Who exactly is our customer? And where do we find them?

Of course, all of this is achieved with essentially no money — and certainly, no money for broad based marketing or advertising. So as there is no capacity for ‘buying customers’ each one has to be found and persuaded one by one.

However, once you’ve established that *there is* a product / service that a given group of customers will use and buy (£££), then the experimentation shifts to the team and new customer groups.

Here are 11 great questions to help you scale your startup faster, smoother and without exhausting yourself and your fellow founders and leaders.

1. What’s Next?

As your startup achieves more and more success, more awards, more recognition, there is a risk of slowing down the innovation and growth. This question helps refocus on what’s coming next, in the immediate future.

2. Can We Go Faster?

It already feels like to you are travelling at the speed of light, but this question allows you and your team to reflect on whether you can achieve more by doing things differently — so you achieve your goals faster, but by running a little slower!

3. Where Do We Want to Be in 12 Months Time?

This is a ‘killer’ of a question for successful startups — you’ve been so focused on the here and now — of making sales, making the product work — that you haven’t been able to look beyond the next 24 hours let alone 12 months. At this stage, 12 months is still in ‘long term goal’ land — but asking the question helps reflect on where this is all going and if its going where you want it o.

4. What’s the Best Thing About What we Have Created?

Stop, admire what you have achieved — its amazing! Then recognise that as you scale, the business will change out of all recognition — so what elements of the startup are most important to you? If you don’t define this early on, you’ll lose those things that are most valuable.

5. What’s Do We Want to Change / Keep About Our Culture?

Now is the time to think about culture. Who you are and how you do things will determine how you hire, who will join and what your scaleup will feel like in a few years time. It will also affect your ability to attract new customers and / or investment if you don’t get this right. This question begins a conversation about a mission critical issue for your scaleup.

6. Where Do We Want to Be in 3 Months Time?

Ask this after the ’12 month’ question! 3 months is still a long time in startup / scaleup land — but this question helps set direction and priorities. Equally, it helps set the ’12 month’ question as a set of values and objectives. You may also find it helpful to ask — what you do you to achieve by Christmas? By Easter? By summer? By Autumn?

7. What if… There Was an Easier Way to Do This?

‘What if’ questions help us think through alternative ways of doing things. Ask for easier ways to do things significantly reduces risk of delivery delays and other risks — so where ever possible, reduce risk by asking is there is an easier way to do things. Sometimes, you have to experiment to find the ‘easier way’ — just be ready for this.

8. What if… There Was a Way to Grow Without Investment?

This is another really important ‘What if’ question. It works well because the received wisdom of startups and scaleups is that raising investment is equivalent to success. It isn’t. Success is whatever you choose to define it as — and, if running and controlling your own successful business is key, then giving away too much equity and power, is unwise.

9. Which is More Important (to each leader): Recognition / Money / Status / Power / Meaning?

This question takes a little time — but it works well when your leadership team each ask this question of themselves and rank the 5 options — top to bottom. It often helps reveal why there are differences of opinion in your team. You can also use this for your top customers / investors — not that you have to ask directly — but put yourselves in their shoes — what are their priorities? It will explain why tensions exist and help you manage them to everyone’s benefit.

10. Who and What is Our Brand

When you startup, the founder(s) is/ are the brand! Your first customers, buy you and ‘why’ you are doing this, rather than the product itself. As you transition to a scaleup, your brand changes, your product brands become the focal point and the founder(s) brand(s) move to the background. Understanding how this changes helps you navigate your marketing messages in a fast changing environment.

11. How Do We Transition to Enterprise / Group / Channel Sales?

Lastly, let’s talk about sales! It if often the case that startups sell direct to small customers / other startups via websites/ automated sales. To grow, bigger deals and partnerships with enterprise sized customers and later corporates is where you growth will come from. This is also true for C2C businesses as you begin selling via channel partners.

Often, the deeper insight comes not just from the initial question, but also finding the right follow up question. If you want some coaching help to land those insight and gain the benefits of faster and smoother growth — just get in touch.

Originally published at https://www.mediamodo.co.uk.

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