The Biggest Point: To coach a challenger sales team through dilemmas effectively, the starting point is their mindset. If a rep doesn’t see themselves as a trusted advisor who challenges conventional thinking, the tactics, techniques, and even the methodology won’t stick. Getting the mindset right creates the foundation for everything else to build on.
This takes me to something I always like to share with any team member or manager which is “The Belief and Success Cycle” from Tony Robbins. It goes:
- Belief: The amount of Belief you have determines the amount of Potential you can tap into.
- Potential: The amount of Potential you tap into determines the amount of Action you take.
- Action: The amount of Action you take determines the Results you get.
- Results: The Results you get determine the Belief in yourself.
When faced with coaching challenges, particularly in a challenger team, the temptation is often to jump straight into fixing behaviours – how someone runs a meeting, the questions they ask, or how they manage objections. But in my experience, those are symptoms.
The root cause? How the rep perceives themselves in the customer conversation. If they don’t see themselves as an equal or even an expert the customer can rely on, everything else falls flat.
Let me give you a perspective that shifted my own approach to coaching. Challenger isn’t about “being difficult” or “knowing more than the customer.” It’s about driving curiosity and creating insight through a blend of confidence and empathy. But that doesn’t happen unless the team believes they’re capable of challenging in the first place.
1. Coaching Mindset Before Behaviour
This is about helping people reframe who they are in the sales process. A lot of reps struggle with stepping into the advisor role because they think it’s about telling customers what to do. It’s not. It’s about showing customers a perspective they hadn’t seen before.
In practice, I would ask one question: “What do you believe your customer would say they need from you to truly solve their problem?” If they say “answers” or “features,” I know we’ve got a mindset gap. But if they say “guidance” or “perspective,” they’re starting to understand that their value isn’t just in the product – it’s in their ability to frame the problem differently.
2. Lead With Curiosity, Not Control
Challenger isn’t about following a rigid playbook – it’s about creating insight, and insight only comes from curiosity. Here’s a question I would ask both myself and any team member I am supporting: Are you asking the kind of questions that make the customer stop and think?
In one coaching session, I worked with a rep who struggled because he went with only serving what they asked for, such as “they just wanted training.” So, we focused on curiosity. I had him ask in an inquisitive style when a customer described what they wanted, Why, “Great so you’re looking to get your team some training, as I always like to ensure we get the best outcome for you do you mind me asking why you are looking for training for the team” It was uncomfortable for him at first, but over time, it helped him uncover deeper pain points. And it worked. He went from transactional to transformational, not by knowing more, but by being genuinely curious. The Why 3 Times approach is incredibly powerful for truly understanding what is driving the customers actions.
3. Teach Emotional Resilience for Tension
The uncomfortable truth about being a challenger is it creates friction. Not everyone is comfortable with that, and that’s okay – it’s a skill, not a personality trait. What I’ve found works best is teaching reps how to read and manage tension, not avoid it.
Something I remind myself and team members I have worked with is that Intellectual Intelligence lets you what to ask, Emotional Intelligence allows you to know when and how to ask it.
A common example I have come across over the years is team members who avoided pushing back on customers because they were afraid of being seen as “too aggressive.” Together, we role-played scenarios where we leaned into empathy first, followed by a confident challenge. It wasn’t about being combative; it was about showing the customer they’d been heard before introducing a new perspective. Over time, they not only handled tension better but actually sought it out as an opportunity to build credibility.
4. Use Peer-to-Peer Coaching to Build Collective Expertise
An approach I regularly take and is effective when coaching teams which has the dual benefit of both taking the pressure off you as the coach and empower the team to coach each other. As Challenger selling isn’t about lone wolves; it’s about leveraging the strengths of the team.
I put into place in my coaching sessions with team members a regular group session. It’s simple: team members bring a real customer scenario they’re stuck on, and the group helps them break it down and build a strategy. The magic here? They learn as much from listening to others’ approaches as they do from solving their own challenges. By ensuring the teams voices are brought to the front and providing a safe and supported environment to engage in the session the result is a team that’s sharper, faster, and more aligned.
5. Celebrate the Wins That Matter
Finally, let’s talk about what we celebrate. Most sales teams focus on the outcome – winning the deal. I would argue (and I do) the most important goal for any B2B team is to win the customer. Winning the customer means deals will come. Challenger is about the process, the moments where a rep challenges a customer’s thinking and creates value.
I would always look for opportunities to celebrate the behaviours and growth of team members as well as the wins. Making this meaning and recognised, rewarding insights shared and mindsets shifted. Focusing on developing the teams mindset and behaviour means they won’t just win one off deals but will win the trust of customers for years to come.
My Key Takeaway
If you want to drive real change in a challenger sales team, don’t just coach the tactics – coach the mindset. Teach them to see themselves as problem-solvers, lead with curiosity, embrace tension, and celebrate the moments that truly matter.
From my experience, this approach has led to significantly more accurate pipelines, better understanding of risks to manage or overcome, and consistently higher performance. These benefits stem from stronger core fundamentals but also from increasing deal sizes by creating additional value and understanding wider customer needs through greater insight into their drivers and plans. Driving growth in your team in this way will create a long-term change for the better.
