How to be a Better Stakeholder

20 questions to ask instead of “When’s it going to be done?”

Dingle Peninsula, Ireland

In my last post “Slow Productivity for the Software Industry”, I suggested that reducing Projects In Progress is a great way to increase velocity and prevent burnout. In getting buy-in to do less at once, I wrote:

Overtime hopefully you can train stakeholders to stop asking questions like “when will we get these 5 projects done?” but instead ask:

“Are we working on the 1–2 best things?”

“Would we still do this project if it took 50% more time?”

“How can we deliver something smaller, somewhat sooner?

This may come as a surprise to some, but your job as a stakeholder isn’t primarily to find out when the work is going to be done! Instead your job is to make the best decisions with the information available and to set the team up to execute your goals successfully.

Teotihuacan, Mexico

So in the spirit of a former boss who said that the best leaders ask the best questions, here are 20 questions stakeholders¹ can ask instead of “When’s it going to be done?”:

1. How can I help you?
2. Do you have the business / product / other context you need?
3. Do you understand my goals with this work?
4. How’s the team’s morale?
5. Where is there still risk and uncertainty in the plan?
6. What did we learn this week?
7. What’s blocking the team?
8. Can you fill out this RAID log?
9. Is giving me updates slowing you down?
10. Is there a sprint/epic/project report being auto generated I can use to follow along?
11. Can we deliver important parts of this work before the whole?
12. What would you do differently with less time?
13. What would you do differently with more time?
14. Should we stop / cancel this work?
15. What are we not getting to as we focus on this work?
16. Are we still doing this work for the right reasons?
17. Can I provide hands-on feedback?
18. What does the rollout plan look like?
19. What are the work’s SLO/SLIs?
20. How should we celebrate when we finish?

There are definitely some themes here for stakeholders: question with empathy and play an active role by being helpful. Putting this list together was a good reminder for me- favor assistance over accountability as an engineering director and stakeholder.

Let me know what you think! What questions do you wish your stakeholders would ask? As a stakeholder, what are your favorite ways to learn what you need?

¹ For our purposes, I will define a stakeholder as anyone with a vested interest in the output of a software engineering team.