Last week, we brought together sales leaders from across different industries for our quarterly dinner. It was a chance to step away from targets and meetings, and have honest conversations about what is actually shaping sales teams right now. The result was one of the most candid evenings we have hosted, with topics ranging from how to assess real sales skills in interviews to the growing role of AI, and the evolving challenges of field sales.
Here’s what came out of those discussions:
The Number One Thing to Look for When Interviewing
The evening began with a simple question: what really matters most when hiring salespeople? Honesty, transparency, integrity, resilience and coachability came up repeatedly as the qualities that make a lasting difference once someone is in the role. The harder part is figuring out how to assess these traits meaningfully during an interview.
One leader explained that they look for candidates who are willing to challenge rather than give a basic response. During the interview, they ask the candidate how they thought it went, not to hear a rehearsed answer, but to see whether the individual can reflect critically and engage in constructive debate. This approach reveals self-awareness, openness to challenge, and a mindset that thrives on development. These behaviours often translate directly into handling sales conversations and managing performance, making it a simple but highly revealing technique.
The Challenge of First-Time Managers
The discussion then moved to first-time managers and the blocks that can appear when top performers are promoted without a clear succession plan beneath them. These salespeople step up because they excelled as contributors, but the professionals they now lead are left without an obvious path of their own. The issue is rarely intentional; it stems from a lack of structure that supports continuous progression.
Several attendees explained how they now avoid promoting anyone into management until there is clarity on who is ready to progress behind them. Others reflected on the value of assigning mentors from within the immediate team, giving aspiring leaders space to practice coaching and gain exposure to development opportunities that don’t solely rely on their manager moving on. The message was clear: suitable profession depends on depth across the organisation, not just upward movement.
Attitudes Towards AI
AI sparked lively conversations, particularly around whether a candidate’s relationship with AI should form part of the interview process. Some leaders already include AI-based tasks because the technology sits at the centre of their sales process, from research to personalisation. Others noted that AI-assisted preparation is completely acceptable as long as candidates are open about how they use it, because transparency is a non-negotiable.
A generational shift is emerging too. Many sales professionals in their early twenties have studied and worked with AI from the outset and carry a natural ease with these tools.
Hybrid and remote working also came up, especially the noticeable drop in energy on Fridays when more people work from home. Some questioned whether team meetings should shift to better match natural working rhythms, while others argued that outcomes matter far more than location, especially for global teams. AI can support productivity, but strong leadership and clear expectations still do most of the heavy lifting.
What Sales Leaders Want From A Recruitment Partner
When the conversation turned to recruitment partnerships, communication, listening and honesty were highlighted immediately. Leaders emphasised the need for realism around budgets and market conditions, and the importance of regularly revisiting job specifications rather than recycling old versions. Markets move fast, and effective hiring depends on understanding what the organisation needs today. A recruitment partner who challenges and refines is far more valuable than one who simply takes a brief at face value.
Field Sales Hiring and Decision Making
Field sales roles promoted some of the most thoughtful conversations of the night. Hiring from outside the industry can be difficult, especially where sales cycles stretch across years. In these situations, revenue history alone does not tell you enough. Leaders spoke about the need to evaluate mindset, aptitude and personality alongside technical experience.
One example involved a business that profiles both its customers and its employees. Their teams observe surgeons in theatre to understand communication styles and stress responses, allowing them to match salespeople to the personalities they will be working with. This creates stronger relationships and helps new hires succeed in high-pressure, highly specialised environments.
The Evolving Challenge of New Business Development
New business acquisition is shifting. Many organisations are dividing responsibilities between field sales and territory management, leaving fewer people focused solely on net-new opportunities. This raises questions about compensation, accountability and role clarity. One guest described a bumpy start to the transition but said stability arrived once expectations were properly aligned. Another shared how they now hire analysts to provide market intelligence and guide where sales teams should focus. This creates a far more targeted approach to new business, particularly in markets where opportunities are harder to surface.
Incentives, Remuneration and Customer Experience
Remuneration naturally led to a discussion on customer experience. Everyone agreed that incentives shape behaviour, and misaligned structures can unintentionally push customers in the wrong direction. If cross-selling is rewarded too heavily, customers may feel pressured. Thoughtfully aligning structures, incentives and business plans with the behaviours the organisation wants to encourage has a direct impact on customer satisfaction and long-term relationships.
A Different Way to Assess Sales Talent
We closed the evening discussing assessment methods. Sales leaders are increasingly moving beyond traditional interview to more practical evaluations that reflect real sales scenarios. Many highlighted the value of assessment centres like those we run, which simulate live selling situations and role plays to evaluate communication, problem-solving, and resilience. This method gives a much clearer picture of how someone will perform day to day, particularly in roles where adaptability and real-world decision-making are critical.
Looking Ahead
The evening made on thing clear. While each individual sales team faces unique challenges, they are not navigating them alone. The hurdles raised around the table are ones many teams are working through right now. Dinners like this give sales leaders the space to reflect, compare experiences, and share ideas that genuinely move teams forward.
Want to join the conversation? Our next dinner is already in the planning stages. Because the best insights happen when we get away from our screens and actually talk to each other.
