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  • Luke Entrup

What Happens in a Leadership Coaching Session?

Have you ever wondered what happens in a leadership coaching session? If so, check out this list.


After beginning work with a new client, I often spend a few months helping them understand how to best use my coaching support. There is a period of presenting options for deeper work together. Over time I’ve started capturing the various topics I’ve worked on with my clients in our coaching.


If you are a curious voyeur or tire-kicker here is a partial list of ways I’ve supported my clients:


  • Prepare you to give feedback to an employee or colleague by providing a specific format, prepping a script, and doing a practice run.


  • Review and provide comments on a pitch deck for potential investors.


  • Help you understand how intense experiences from your past impact how you are leading your company and creating your life and then work towards integrating them.


  • Prepare you to ask for a new title and/or a raise.


  • Overhaul your schedule to get more focused on the most important things.


  • Give personalized meditation and yoga practices for your unique body and mind.


  • Conduct interviews of your closest collaborators and give you actionable feedback about how you are perceived by those around you.


  • Provide support and structure to consciously end a relationship with a long-term life partner.


  • Help you envision and map out your ideal leadership team to help scale your business, then support you as you execute the hiring and onboarding plan.


  • Help you bring more passion and juice into their marriage.


  • Prepare you to compassionately fire an underperforming employee.


  • Help you let go of the burden of leadership in a way that honors your desire for ease and abundance.


  • Help process and make sense of losing a loved one.


  • Support women entrepreneurs as they navigate the mine-field of gender dynamics and sexism in their field.


  • Provide thought-partnership and skills on how to deal with assholes in your company.


  • Facilitate conversations and repair between feuding co-founders.


  • Craft a plan to deal with the cultural aftermath of sexual harassment in a company.


  • Receive and revise the structures used for meetings throughout the organization. Provide templates for 1:1 and team meetings.


  • Help create a culture that is safe and ready for a more diverse workforce.


  • Help you see blindspots in your leadership style that are limiting your effectiveness.


  • Help you to become more aware of how your emotions provide vitally important information for leading your company.


  • Helping you think about ways to vet potential investors, board members, and advisors.


  • Help you use the work of running a company as a path to self-awareness.



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