The Five Toughest Coaching Conversations We’ve Simulated This Year

The first quarter of 2025 has been one of the most challenging and volatile times for business ever. Markets are down, there is tremendous uncertainty, and we still have the raging debate of working remotely vs. working in an office. At the same time, the pressure to perform has never been higher.

One of Advantexe's largest growing areas of work during this time has been our customized coaching simulation business. We have seen a significant increase in requests for both skill-building and practice simulations in coaching, and the types of scenarios have been very complex and difficult.

A skill-building simulation scenario is a multi-layer, decision-tree situation in which the learner engages in a simulation scenario and weaves through alternatives, building the skill along the way. A practice simulation is an AI-driven conversation in which the learner practices a specific coaching skill.

Five Most Challenging Coaching Conversations

Without giving away any confidential client information, I thought it would make for an interesting blog post to share the titles and topics of the five most challenging coaching simulation scenarios we have developed in Q1, 2025:

An employee feels they are going to be replaced by AI

How do you coach an employee who comes to you fearful of losing their job to an AI replacement? As more companies realize the efficiencies of AI, this will be a significant issue.

Coaching employees through a business spin-out / acquisition

Another new reality is this is never going to stop. Large companies will spin out business units, and large companies are going to make acquisitions. How do you coach employees who are going through either and keep them productive and motivated?

Dealing with the realities of the DEI executive order

This one is challenging and has impacted millions of people and their companies. Employees are confused, unsure of who to trust, and feel like we have taken a step backward. How do you have a conversation with an employee telling them that they are no longer in a Business Acumen for Women Leadership program because the program doesn’t exist anymore?

Practicing these types of conversations is extremely emotional and requires great practice.

Burnout

As the new realities of defining work are taking their toll on many employees. They are feeling overwhelmed, tired, and burnt out. How do you have a coaching conversation to either re-engage and motivate them or help them exit the company for a different job opportunity?

Geopolitical disruptions of the supply chain

I saved this one for last because it is the most requested coaching simulation scenario. I have written and modeled several different variations of this scenario, so I will close this blog with some insight into building and practicing the coaching skills related to this difficult dialogue.

The Situation

You are a Supply Chain leader, and one of your direct reports is upset and frustrated by delays in the raw materials needed to manufacture your best-selling product, Goodular.

You want to have a positive coaching conversation, with the primary focus of developing a solution to the supply chain issues and building the employee's confidence.

Here is the best practice model we used in one of the simulation scenarios:

Step One: Clarify the Impact and Broaden Strategic Thinking

• Coaching Point: “Let’s walk through exactly how these tariffs affect our supply chain—what’s the direct impact on costs, lead times, or vendor reliability?”
• Purpose: Help the employee articulate the problem clearly, identify patterns, and start thinking about second- and third-order effects. Encourages a systems-level view.

Step Two: Explore Adaptive Solutions and Partnerships

• Coaching Point: “What alternative suppliers, sourcing strategies, or internal process shifts could we consider to reduce exposure or improve agility?”
• Purpose: Shift the focus from reacting to innovating. Encourages proactive thinking, growth mindset, collaboration, and resilience-building.

Step Three: Support Decision-Making Under Uncertainty

• Coaching Point: “What’s within your control right now, and where do you need support or escalation to move forward?”
• Purpose: Empower the employee to act decisively within their scope while flagging where strategic leadership or cross-functional alignment is needed.

Step Four: Build and Execute an Action Plan

• Coaching Point: “Now that we have some positive ideas, will you build and execute an Action Plan? Let me know how I can support you.
• Purpose: It shows that you want the employee to take action and will be there to support and help the employee's needs.

In summary, these coaching conversations will get harder and more complex. The more you invest in the skills and practice to address them, the better your performance will be.