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Why you should not focus on keeping stakeholders happy
Ever since I entered the software workforce, I’ve always seen managers stressing the fact of keeping stakeholders happy and managing their expectations. As a graduate in a traditional top-down environment, I never challenged their practices, but now after decades of experience and mindset shifts, it doesn't make any sense to me.
Happiness is subjective, what brings happiness to you may not hold any value to others. For example, a prisoner finds no solace in a golden cage other than setting oneself free.

Happiness varies with the environment in which one lives, some survive whilst some thrive. One size doesn't fit all.
Nevertheless, as humans, we love the feeling of being informed. In order to communicate the right information, we need to shift one’s focus from idealistic measures to realistic ones.
Growth happens when we stop assuming and start asking. What you don't ask, is what you never get. Being stupid for a minute is always better than being stupid forever.
So start by asking your stakeholders,
- What according to them is a good level of engagement?
- If they had to improve one area right now, what would that be?
- What interests them?
- What is their view of the team?
- What are their goals and purpose?
- How would they like to be communicated?
Here are some helpful visuals created by Information Artist that you can refer to and turn into brainstorming exercises.

First, begin by identifying the category of stakeholders involved in your product or service. They may belong to any area in your business, ranging from vendors to investors, from influencers to customers.
Once you have categorized your stakeholders into relevant entities, it's time to identify their influence on your product/project or business. The matrix I have illustrated below will help you with this task.

This is the most popular matrix of influence for stakeholder analysis. It was originally published in Making Strategy: Mapping Out Strategic Success by Fran Ackerman (Author), and Colin Eden (Author).
Whilst brainstorming any of the exercises mentioned above, do not forget to involve your stakeholders. They’re an amazing bunch of humans just like us with different motives. All they need is your collaboration, shared understanding, and information, not at the end, but frequently.
One thing I’ve learned through my experience is “Focus on keeping your stakeholders informed, and happiness will follow.”
Don’t burn your energy worrying under assumptions. Use it liberally to build trust and collaborate towards common goals.
Would you rather choose to work with them or work for them?
Don’t forget to let me know how the above-mentioned methods have helped improve your conversations. Keep learning & sharing.

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