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Jack Daly Sydney 2019

Leader to Leader: Greatest Business Pain Points

The results of our survey from Winning Sales Strategies.

At our recent sales workshop with Jack Daly, Winning Sales Strategies, we asked attendees:

What is your greatest business pain point?

We received over 100 responses, all of which have contributed to the latest article in our Leader to Leader series, developed to provide insights for and about leaders.

The Results

  • 15% of responses covered issues surrounding recruitment, including attracting talent and hiring ‘A’ players, making it the number one response.  

  • Culture, including people management and teamwork, was the next most popular choice, with more than 13% of respondents listing it as their number one pain point. 

  • Sales and client management were tied for third place, with each being listed as a key issue for 10% of Winning Sales Strategies delegates. 

Finding the Right People

For most, discovering that recruitment is the number one pain point for our community of business leaders will come as no surprise. The need to find the right people cuts through all companies and industries, and can make or break a business if not properly handled. One of the responses highlighted the need for not only attracting the right talent, but retaining it: 

“Recruiting and retaining key staff.”

This idea of keeping employees; cultivating their talents, challenging them and empowering their best work, made the stress around recruitment clear. 

Culture, or Lack Thereof 

Corporate culture was a concept popularised in the '90s, but has grown to become an integral part of organisational health in many modern companies. Paying lip service to an idea and putting in the time to make it a reality are two very different things, made more complicated by a lack of agreement on what a ‘good’ culture looks like. One response highlighted this issue: 

“Organisation thinking the culture is good - It is NOT.”

The Customer is Always Right

Identifying ideal clients, dealing with customer cancellations and delays, securing face-to-face meetings and contact continuity were some of the other obstacles faced by the Winning Sales Strategies delegates. 

“Customers want more for less.”

While a common adage tries to convince us that the customer is always right, it’s certainly true that the customer is always unique, each one with their own needs, expectations and demands. 

During his Australian seminar series in 2017, best-selling author Simon Sinek shared with audiences tips to understand their customers, all through the lens of The Tipping Point concept. Watch his video here, and secure your seat to his upcoming workshop here.  

Other Pain Points

Sales training, time management and execution were other prevalent responses.

Sales training was an unsurprising result, given those who responded were winding up a full day with sales guru Jack Daly. A common theme throughout the day training, many attendees felt that finding prospects was difficult, but knowing what to do with them was sometimes even harder, as was finding the appropriate tools to close the deal.

The Execution Framework 

Time management and execution were also listed, concepts that are in many ways linked. 

Franklin Covey's Chris McChesney, co-author of the well-known book on the topic, 4 Disciplines of Execution, has spent a career dealing with this problem. Many leaders have great ideas, a solid strategy and plenty of enthusiasm, but no real execution framework to get their work over the line. 

His four-step system has been developed to provide a simple and repeatable formula to track progress, manage accountability and execute on essential priorities. It gives leaders the greatest gift there is: the time and energy to spend on key tasks and priorities. 






Communication breakdowns, both internally and externally, admin overload and leadership were other notable pain points mentioned. Our recent livestream with Trillion Dollar Coach authors Jonathan Rosenberg and Alan Eagle highlighted the power of clear communication and effective leadership, speaking of their time with coach turned mentor Bill Campbell. Jonathan shared how Bill gained the trust of his employees:

“He let people see his own vulnerabilities and they shared their own. He understood the dynamics of how to pull people together as members of a team.” 

During her sell-out tour of Australia, Brene Brown shared this sentiment, talking extensively about brave leadership, choosing courage over comfort, and the power of vulnerability. Read more here

Key Learnings

We recently asked the question: What is your greatest business pain point?

The pain points of our sample of Australian business leaders were as diverse as they are, dictated by their industries, business types and seniority. What was clear, however, was that issues related to people; recruiting them, training them and traversing the culture that’s influenced by them, were felt by almost all.  

But let’s assume you can overcome this barrier, and your recruitment process is ready. Once the right people are in place, then you must answer the bigger question: How do I ensure they execute on our key strategic priorities? As with all things, it’s not simple.

As leaders, the best we can do is always be open to learning, improving and iterating, whether it means simply hearing a different point of view or starting over with an entirely new business system. You've told us your pain points, now it's time to make a change. 


Execution expert and Wall Street Journal's No. 1 best-selling author, Chris McChesney will be in Australia next month, returning to present his famous workshop, 4 Disciplines of Execution. Learn what all the fuss is about: tickets on sale here.