Why Insight Alone Won’t Change How Leaders Lead
Senior leaders are not short of insight. They have attended programmes, read books, listened to podcasts and had plenty of “lightbulb moments”.
The problem is not knowing what to do differently – it’s consistently doing it when the pressure is on.
That’s why, when you’re deciding how to choose executive coaching services, one of the most important questions to ask is:
How much of this coaching is conversation, and how much is deliberate practice?
Coaching that never leaves the room can feel powerful but change very little. Coaching that builds in practice – on real deals, decisions and interactions – is far more likely to shift behaviour and performance.
The Difference Between Reflective and Performance Coaching
Most executive coaching has a reflective element. Leaders step back, think about patterns in their behaviour and explore new perspectives. That’s valuable – but incomplete.
For revenue leaders, the coaching that moves the needle treats leadership as a performance discipline, not just a topic for reflection. It looks more like:
- Preparing for specific meetings or conversations.
- Rehearsing critical interactions before they happen.
- De-briefing what actually happened and adjusting the playbook.
In other words, it builds the same kind of practice habits we expect from elite athletes, musicians or presenters – but applied to leadership.
When evaluating providers, you’re trying to understand where they sit on this spectrum and whether their approach matches the outcomes you identified in Step 1.
What “Practice” Should Look Like in Executive Coaching
Practice in coaching is more than “try this and let me know how it goes”. Strong providers will design structured practice loops into the coaching journey.
You should expect to see elements such as:
- Role-plays and simulations
Rehearsing upcoming conversations – a pipeline review, a board update, a pricing negotiation – in a safe environment, then refining the approach.
- Real-play with live deals and decisions
Working on actual opportunities, strategic customers or internal decisions, not fictitious case studies.
- Specific experiments between sessions
For example: “In your next three 1:1s, ask these questions and observe what changes,” followed by a debrief.
- Feedback loops
Encouraging leaders to gather targeted feedback from their teams and stakeholders on particular behaviours they are practising.
- Use of tools and prompts
Checklists, conversation guides or short frameworks that make new behaviours easier to execute under pressure.
The key is that practice is intentional, repeatable and tied directly to the behaviours and outcomes you care about.
Connecting Coaching Practice to Revenue Moments That Matter
In a revenue organisation, some moments have an outsized impact on results. For example:
- How leaders run pipeline reviews and forecast calls.
- How they handle strategic deal reviews and go/no-go decisions.
- How they show up in QBRs, board updates and investor conversations.
- How they coach first-line managers and account teams.
An effective coaching partner will focus practice on these high-leverage moments.
Ask potential providers:
- Which moments that matter do you typically focus on with revenue leaders?
- How do you build practice around those moments?
- Can you give examples of how coaching changed the way a leader ran a specific meeting or handled a critical deal?
If they talk mainly about mindset and self-awareness without ever mentioning concrete situations, that’s a sign the practice element may be thin.
The Role of Digital Practice Tools
Many organisations are now exploring digital practice tools alongside traditional coaching – for example:
- AI-powered role-plays where leaders can rehearse conversations and receive feedback.
- Interactive scenarios that simulate buyer or stakeholder reactions.
- Digital “experts” or nudges that provide just-in-time prompts before key meetings.
These tools can’t replace human coaching, but they can:
- Increase the volume of practice between sessions.
- Provide consistent scenarios across a cohort of leaders.
- Generate data on where leaders struggle or improve.
When considering a coaching partner, ask:
- Do you use any digital practice tools as part of your approach?
- How do you ensure these tools align with our sales methodology and culture?
- How is data from these tools handled, and how do leaders access their own insights?
If you prefer a fully human approach, that’s fine – the key is that practice still exists, even if it’s low-tech.
Integrating Practice With Manager Cadence
For practice to stick, it needs reinforcement beyond the coaching room. That’s where line managers and operating rhythm come in.
Stronger coaching providers will actively look to connect practice with:
- Regular 1:1s between leaders and their line managers.
- Deal and pipeline reviews where new questioning and coaching behaviours can be tested.
- QBRs and leadership meetings where leaders can practise new ways of framing data and decisions.
Ask providers:
- How do you involve line managers in the coaching process?
- Do you provide guidance for managers on how to reinforce what’s being practised?
- How do you stop coaching becoming “something separate” from the day job?
If practice is confined to the coaching conversation itself, behaviour change is likely to be slow and fragile.
How to Spot Whether a Provider Really Values Practice
Beyond what’s written in proposals, there are some practical signs that a provider genuinely prioritises practice:
- Their case studies talk about specific behavioural shifts in real situations, not just generic feedback scores.
- Coaches are comfortable getting into the detail of deals, meetings and conversations rather than staying abstract.
- They offer sample sessions that include rehearsal, feedback and experimentation – not just discussion.
- They talk openly about the effort required from leaders to practise, not just the inspiration they’ll receive.
You can also ask to sit in (or receive a recording of) a demonstration session that shows how they work with practice.
Questions to Use When Evaluating the Practice Element
Here are practical questions you can use in RFPs or provider interviews:
- How do you ensure that coaching leads to concrete behaviour change, not just new insight?
- What kinds of practice activities do you typically build into coaching for CROs, regional VPs or Heads of Sales?
- Can you share examples where practice in coaching changed the way a leader ran a specific meeting or handled a strategic deal?
- How do you encourage leaders to practise between sessions, and how is that tracked or reviewed?
- Do you use any digital tools or simulations to support practice? If so, how do they fit into the overall coaching journey?
- How do you involve line managers in reinforcing and sustaining new behaviours?
The aim is to move beyond “we ask powerful questions” to a tangible picture of what leaders will actually do differently.
How Step 6 Strengthens Your Overall Decision
Looking for practice, not just conversation, is a crucial part of deciding how to choose executive coaching services.
When you combine this step with:
- Clear outcomes (Step 1).
- A defined audience and context (Step 2).
- The right mix of coaching formats (Step 3).
- A robust methodology (Step 4).
- Real sector expertise and commercial acumen (Step 5).
…you dramatically increase the chances that coaching will show up in the way leaders run their teams, deals and decisions every day.
In other words, you’re not just buying better conversations – you’re investing in better performance.