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The Empathy Challenge

Updated: Feb 27, 2023

As the summer months approach, you may be planning to invest more time in your own development, and to sharpen some of your technical or leadership skills. For many of us, the past few years have been especially challenging to navigate. Whether you have been adjusting to a new hybrid work environment, starting a new role, or re-examining your goals and priorities, this summer can mark a great time to re-set and re-focus.

This opportunity to re-set also aligns with recent research about the need to transform how we coach and inspire the teams around us and strengthen our ability to be a more connected and caring leader. If the last few years have taught us anything, demonstrating empathy is a critical skill.

Recent data and insight collected from Josh Bersin suggests that leaders across all industries should be putting more emphasis on empathy-focused skills. Bersin suggests a revised set of leadership skills (1), so that we move from a place focused entirely on business results, towards a more human-centered approach.

Here are some examples:

  • Instead of focusing on hitting the numbers and incentivizing when numbers get achieved, put more focus on inspiring the people around you to achieve their goals. Drive a culture where people feel connected and inspired.

  • Avoid zeroing in on errors and failures and move towards creating a sense of safety where you and your team can test, share and learn. Create a space where new ideas are welcome.

  • Rather than showing up as knowing all the answers and role modelling strength and execution at all costs, demonstrate vulnerability. Showcase how rest, wellbeing and building resilience is critical to your success.

So, what are some strategies you can test out to fine-tune your skills to inspire, connect and bring a greater focus on empathy? Here is a simple summer challenge that may spark new learning.

Challenge #1: 60 seconds of silence.

Try this simple exercise. When you are meeting with a team member during a 1:1, or having a project update with a colleague, ask an open-ended question to seek their perspective on how things are going. Without interrupting or interjecting, remain silent for 60 seconds. In fact, if there is slight discomfort about the awkward silence, even better! By allowing this moment of quiet reflection, you are giving the other person a rare opportunity to be heard and understood. With our frantic pace and workload, 60 seconds of silence may bring more insight and reflection than you think.

Challenge #2: Ask a “what” question.

How many times have you asked questions like “Do you have any questions?” or “You’re ok with this plan, right?” or “Any issues here?” These closed-ended questions are conversation enders and often only serve the purpose of ending a meeting quickly.

To re-set your approach, ask a question which can demonstrate that you really do want to hear more about another person’s perspective and ideas. As part of your challenge, test out using one of these “what” questions:

  • What is the real challenge you’re facing?

  • What is your perspective on this?

  • What is one thing we could do differently right now?

  • What have I missed or overlooked?

  • What support do you need from me?

Challenge #3: Carve out 30 minutes for a brainstorm.

If you’re like me, you have a deluge of deadlines and projects constantly on the horizon. Carving out time to think and collaborate can have huge returns for time-strapped leaders and can also create a better sense of purpose and connection across a team. For this challenge, set up a 30-minute brainstorm session with your cross-functional partners, colleagues, or team members. The focus of the meeting is simply to map out, whiteboard, and talk through different ways to solve a problem. Creating an intentional space to learn and share ideas is a remarkably easy way to connect and gain insight from those around you. Spending time with a coach to test out your ideas with an unbiased thinking partner is another great way to start.

Are you up for the challenge? In the spirit of sharing ideas, feel free to connect with me on LinkedIn or share in the comments what you’ve been testing out.


1. Big Reset Playbook: Human-Centered Leadership, Josh Bersin, 2021


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