8 Powerful Questions You Need to Ask Before Engaging With Your Executive Career Stakeholders

Stakeholder engagement is one of the more critical aspects of successful executive career management. Such stakeholders can be anyone from the Board of Directors of a company you would like to hire you, to someone you’re serving with on a committee in your association who can connect you to a potential career advancement opportunity. Your relationship with them is dynamic and can change over time.

man-with-questionsThere are many advantages to identifying and getting to know your stakeholders, and even more disadvantages to not engaging with them. A failure to understand their needs can lead to blindspots for executives, which can be a career-limiting move.

On the other hand, effective engagement can result in fast career progress. You can use research-based strategies to notice such blindspots so we can overcome them.

Identifying Your Key Career Stakeholders

While you might be inclined to start engaging with all of your career stakeholders immediately, it would be more practical to focus on the relationships that matter the most. This means sitting down by yourself or with a mentor or coach, coming up with a list of all stakeholders, and then whittling down this list to the people who have the most impact to your career – these are your key stakeholders. Even though it might be tempting to address the concerns of all your stakeholders, limited time and resources mean that you will accomplish more by addressing a targeted list.

When determining who your key influencers are, look for these three attributes:

  1. The stakeholder has a significant impact on your career progress. This means that the long-term success of your career hinges on a continued relationship with this individual.
  2. The stakeholder cannot easily be replaced. From a very connected networker to a well-respected senior executive, you can identify who this stakeholder is by assessing past performance.
  3. The relationship is mutual: you can clearly identify what you need from the stakeholder and vice versa. Your goals and desired results are well-aligned with those of this individual, or can be made to be well aligned through your efforts.

Be Prepared by Doing a Pre-Engagement Assessment Using These 8 Questions

Regardless of the urgency, do a pre-engagement check before you engage with your key stakeholders directly on any given issue. This will prepare you for the meetings and lead to a productive discourse.

Otherwise, you might fall into the dangerous judgment error known as the false consensus effect, where you assume other people are more similar to you and more inclined to do what you want them to do than is really the case. The false consensus effect is just one out of over 100 mental blindspots that scholars in cognitive neuroscience and behavioral economics call cognitive biases.

The questions below are informed by cutting-edge neuroscience research on how to address these cognitive biases, along with my own experience of over two decades coaching and training executives on stakeholder engagement.

  • What are their feelings, values, goals, and incentives around this issue?
  • What is their story around this issue?
  • What is their identity and sense of self as tied to the issue?
  • How are they the hero in their own story?
  • Why should they want to listen to your message and do what you want?
  • What obstacles would prevent them from listening to your message and doing what you want?
  • How can you remove the obstacles to and increase the rewards for them listening to you and doing what you want?
  • Who do you know that can give you useful feedback on your answers to the previous pre-engagement assessment questions?


Your relationship with your career stakeholders will change over time and you will face different issues at varying difficulty levels. However, by learning how to identify your key stakeholders and doing pre-assessment checks before engaging with them, you will be able to have productive discussions and grow deeper relationships.

ExecuNet VIPs can watch the author’s  recorded ExecuNet Master Class, “How to Avoid Disasters in Managing Your Career.”

Dr. Gleb Tsipursky

Dr. Gleb Tsipursky

An internationally-renowned thought leader known as the Disaster Avoidance Expert, Dr. Gleb Tsipursky is on a mission to protect leaders from dangerous judgment errors known as cognitive biases by developing the most effective and profitable decision-making strategies. A best-selling author, he wrote Never Go With Your Gut: How Pioneering Leaders Make the Best Decisions and Avoid Business Disasters (Career Press, 2019), The Blindspots Between Us: How to Overcome Unconscious Cognitive Bias and Build Better Relationships (New Harbinger, 2020), and Resilience: Adapt and Plan for the New Abnormal of the COVID-19 Coronavirus Pandemic (Changemakers Books, 2020). He has over 550 articles and 450 interviews in Inc. Magazine, Entrepreneur, CBSNews, Time, Business Insider, Government Executive, The Chronicle of Philanthropy, Fast Company, and elsewhere.

CBS News, Time, Business Insider, Inc. Magazine, and elsewhere. His expertise comes from over 20 years of consulting, coaching, and speaking and training experience as the CEO of Disaster Avoidance Experts, and over 15 yearsin academia as a behavioral economist and cognitive neuroscientist.

Contact him at Contact him at Gleb[at]DisasterAvoidanceExperts[dot]com, follow him on Twitter @gleb_tsipursky, on Instagram @dr_gleb_tsipursky, and on LinkedIn, and register for his free Wise Decision Maker Course.

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