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Thank you to the 1,400 leaders who’ve generously done the 7 questions!
I hope reading

helps you in your leadership.



Jonno White

7 Questions with Stephen Cummings
7 Questions with Stephen Cummings

Name: Stephen Cummings

Current title: Managing Partner

Current organisation: Rizolve Partners Inc.

Stephen is a leading advisor and financial expert who works with private Business Owners to drive value and to put in place transformational strategies that position businesses for exit on optimal terms.
He has a successful track record in the Canadian Private Equity and Venture Capital Industry, managing large portfolios of private companies developing growth strategies, executing transformations and achieving numerous liquidity events. He has international credentials being a qualified CPA, CA in Ontario and is an FCA in England and Wales.

Prior to founding Rizolve Partners, a leading strategic business advisory firm to the SME market, Stephen was a leading executive with a top quartile Private Equity firm DRI Capital and a Partner with Lumira Capital, one of Canada’s leading Venture Capital firms. Before applying his skills in private capital, Stephen was the CFO at Harlequin Enterprises, a global publisher, and qualified as a CPA and Chartered Accountant with Deloitte in London, UK.

Stephen is a member of the Board of Directors of the Ontario Genomics and Chairs its audit and Special committees.

He is also a sought after international speaker

7 Questions with Stephen Cummings

1. What have you found most challenging as a leader of a small or medium enterprise?

I think that the biggest challenge for a leader of a SME business is the need to multi-task whilst driving Sales that bring in Cash. The trick I believe is to have a laser focus on what is important to move the Organization ahead and to not get distracted by the issues of the day that will always be there.

2. How did you become a leader of an SME? Can you please briefly tell the story?

Rizolve Partners is a team of professionals that have been put together to help Business Owners build transferable value in their business in order that when the time comes they can monetize their greatest asset on their own terms.

3. How do you structure your work days from waking up to going to sleep?

I have always been an early riser and get to my desk early. I really value the 2 hours or more before the calls come in and I try not to look at my email until after 8am (and not after 9pm) as I value a good night's sleep and arising fresh for the following days free!

4. What's the most recent significant leadership lesson you've learned?

The most significant leadership lesson that I have learnt is the applying the concept of Value in building and optimizing a company. Many Business Owners believe that increasing Sales, cutting costs or acquiring other companies is the way to increase the value of their business. Done correctly that may be right. However, all too often it leads to unintended consequences and in certain instances can destroy value. So understanding the concept of improving Quality and doing so in a balanced way so that the economic engine is sustainable, predictable and free of dependencies are very important concepts to learn for many companies.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

The Alchemy of Growth by Baghai, Coley and White

This is a book that demonstrates practical insights for building the enduring Enterprise by 3 former McKinsey partners. The Strategy is one that we applied at a global organization that I was the CFO in and the strategies espoused were very helpful to the growth of that organization.

6. How do you build leadership capacity in an SME?

I believe that the way to approach building leadership capacity in an SME is to understand what disciplines are most critical to building the business for its stage of development and finding the right people to fill those spots both internally and externally in a timely manner. I also think that it is very important to incentivize those key people by rewarding the performance that will move the Organization ahead in a meaningful way.

7. What is one meaningful story that comes to mind from your time as a leader of an SME so far?

The story that is important is one that dwells on the concept of "Cash is King''. A business that is a roaring success but runs out of money without the appropriate financial or equity backing is a failure. One CEO once said to me on this topic that he was surprised that when things get bad the height of the cliff that you can topple off can be very high and the plunge to the bottom can happen very quickly when you finally take a step too far in the wrong direction. Building good long term relationships with stakeholders, financiers, investors, customers, Suppliers and Employees goes a long way when the going gets tough and can be the antidote you need when things don't go the way you planned.

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