Last week, we brought together sales leaders from across different industries for our quarterly dinner. It was an opportunity to step away from the day-to-day and have open conversations about what’s really shaping sales teams today.
The evening’s discussions covered a wide range of topics, from how to retain graduate talent beyond the first year, to the growing role of AI in the sales function, and the ways leaders are thinking about motivation, incentives, and employee engagement.
As always, the value came from sharing real experiences. What’s working, what’s not, and where small changes are making a meaningful difference to performance and culture.
Here’s what emerged from the conversations:
Retaining graduate talent beyond year one
One of the first topics on the table was a familiar challenge for many: you’ve hired a strong graduate, but how do you keep them engaged into their second year and beyond?
The conversation quickly moved beyond perks and into structure. Sales leaders highlighted the importance of showing clear progression early on, not just in theory but in a way that feels tangible. Breaking development down into small, achievable steps helps individuals see progress in real time, rather than feeling like they’re working towards something distant.
There was also a strong focus on helping people buy into the wider vision. When individuals can see how their role contributes to the bigger picture, and when that journey is mapped out clearly, engagement tends to follow. Without that clarity, even strong hires can begin to lose direction.
Motivation, transparency, and human connection
Motivation continues to be closely linked to clarity and honesty, particularly during the hiring process. Several leaders reflected on the risks of overselling roles, noting that being upfront about what a job is and isn’t leads to better long-term outcomes.
Some organisations are now inviting candidates to spend time speaking with potential colleagues before accepting a role. This gives a more realistic view of the environment and helps set expectations early.
The conversation also returned to client relationships. While many leaders are encouraging a more face-to-face interaction, there’s still some reluctance within teams to step away from virtual communication. But the consensus was clear: when in-person meetings do happen, they often lead to stronger relationships and higher-value deals.
At the same time, there was recognition that not all relationships require the same approach. Building rapport virtually can still be effective, particularly in more transactional environments. The key is understanding when to lean into human contact and making it a deliberate part of the sales process.
The role of AI and the risk of stepping back
AI prompted a lively and, at times, cautious discussion. While most leaders acknowledged the value AI can bring to the sales process, there was a shared concern around over-reliance.
Several leaders noted that salespeople are increasingly leaning on AI for answers, sometimes at the expense of their own judgement. In some cases, this leads to individuals unintentionally stepping back from the role they’re meant to play.
The balance is still being worked out. AI can enhance productivity and provide useful insights, but it cannot replace human understanding, particularly when it comes to building relationships and making nuanced decisions. The message was clear: AI should support the salesperson, not become the salesperson.
Making employee surveys meaningful
Employee surveys divided opinion. Some see them as little more than a collection of wish lists, while others view them as a valuable tool for understanding what really matters to their teams.
The difference often comes down to how they’re structured. Leaders who are seeing value from surveys tend to be more deliberate in the questions they ask, focusing on areas that can lead to actionable insights rather than broad or open-ended feedback.
There was also discussion around identifying small, low-cost changes that can have a positive impact on performance. When individual feedback is aligned with company objectives, it becomes easier for employees to see how their input contributes to wider success.
Incentives, bonuses, and behaviour change
Incentives sparked a wide range of examples, from straightforward quarterly commission plans to more creative rewards to drive specific behaviours.
One example that stood out involved a low-cost, experience-based reward that was tied to clear behaviour criteria rather than just performance rankings. Interestingly, the top performer didn’t win, but engagement across the team was high because the goal felt both achievable and genuinely exciting. Sometimes the most effective incentives are the ones people least expect.
Bonus structures also came under scrutiny. Annual bonuses linked to overall company performance can encourage cost-conscious behaviour, but when the calculation lacks transparency, employees can struggle to see how their individual efforts contribute. Clarity remains key to maintaining trust and motivation.
Skills-based recruitment and assessing drive
The final discussion point focused on recruitment and the challenge of assessing qualities like drive and proactivity. These are traits that candidates can easily talk about, but much harder to evidence.
Sales leaders shared the need to move beyond surface-level answers and find ways to test these behaviours more practically. Whether through deeper questioning, real-life scenarios, or alternative assessment methods, the goal is to understand how someone is likely to perform, not just how they present themselves in an interview.
As expectations of sales roles continue to evolve, so too must the way organisations identify and evaluate talent.
The value of conversation
What stood out most from the evening wasn’t any single topic, but how much common ground there was. Leaders from different industries, team sizes, and markets are all working through the same questions
That’s what makes these in-person dinners so valuable. Not just the answers, but the conversations themselves.
Want to join future conversations? Our next Sales Leader Dinner is already in the planning stages. Get in touch with one of our specialist consultants to find out more.
