Saying yes to having hard conversations with Executives

change management confidence stakeholder engagement May 03, 2026
Lata Hamilton in white top smiling; text: say yes: hard conversations with executives

How do you have hard conversations with Executives? Often the change you’re leading is a business critical transformation and that’s why the organisation or the client has invested in Change Management support. But influencing at those senior leadership levels can feel daunting and scary.

 

I say this often: senior leaders and executives may not have gotten to their role through leadership talent or qualities. They unfortunately usually get there through what I call the 3 T’s:

- tenure (length of time at the organisation)

- technical skill (they know how to do stuff, but not lead people)

- nepotism (which doesn’t start with a T but has a T in it, they were promoted by people they know or through internal politics). 

 

Which means that a lot of leaders and managers are TERRIBLE with accountability, for themselves and their teams: they don’t set KPIs, they don’t measure progress, they don’t want to find the root cause or the answer, and almost none know how to have difficult conversations around performance, pay, roles, responsibilities, behaviour, etc. It’s one of the top things that I see as a root cause for change failure. They can sometimes be more emotional and child-like and ego-driven and useless on follow through than employees. 

 

When you need to have hard conversations with Executives there’s two things to remember and balance:

- Their seniority is their status symbol so respect it

- They are just a regular person so keep them in perspective

 

Give them the power they need but don’t give them more power than they deserve.

 

Now you’ve got that down pat, here’s a step-by-step guide for having hard conversations with Executives:

 

  1. Talk with your Project/Program Manager, Sponsor, Head of Change or Client Contact beforehand to know they will back you up.
  2. Ideally set up a 1:1 meeting before any group Executive meeting.
  3. Paint a picture of the problem or the depressing future and most importantly, the impact to them as an individual and to their team, or better yet ask probing questions to get them to articulate this.
  4. Ask if they want help with the solution (this puts the ball back in their court).
  5. Run the workshop or present the solution.
  6. Get commitment on the steps / actions you will take and they will take.
  7. Set the next check in.



Holding your own when having a hard conversation with an Executive is critical if you want to be taken seriously as a trusted change advisor with influence and impact. My free Change Advisor Bootcamp shares more practical and powerful tools and tips to shining in your Change Management expertise at any leadership level. 

 

CLICK HERE to register for instant access to my free Change Advisor Bootcamp

 

Lata xx



P.S. My Change Advisor Bootcamp is completely free to watch but access won’t be available for long. If you want to learn my practical and powerful tools and tips to shining in your expertise as a trusted change advisor with influence and impact, watch the free workshop here now.

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