How’s That Working for You?

During my client work I am frequently presented with a description of some approach a team or organization is taking when applying agile. I am then often asked for my opinion on that approach. I most frequently respond by asking the following question: “How’s that working for you?

I believe this question is an excellent first response to a query for feedback on an approach or a statement of how something is currently being performed.  Let me explain why.

Coaches Should Ask Thought-Provoking Questions

I approach coaching from the prospective of I’m not here to give you answers; I am here to help you find answers. As such, I believe a good coach (like a ScrumMaster) rarely offers a direct answer to a question. Instead, a good coach frequently responds with questions that encourage dialogue and discussion. “How’s it working for you?” is an example of a just such a question.

Invites a Deeper Conversation

Asking how something is working is an invitation to engage with me in a deeper conversation on the topic. If I just provide a quick response with my opinion on the other person’s situation, he might simply accept my response as somehow being authoritative, which might end the discussion.  If I instead query the other person for important information, it promotes a deeper conversation the topic.

Forces Introspection

Asking how something is working forces introspection. It solicits a self-analysis of how the approach is working. Sometimes people have given the situation thoughtful consideration and can quickly provide their opinion on how things are going. However, many times people haven’t yet invested the effort to examine the situation and might be hoping that I can save them the trouble by giving my opinion. Asking how’s it going forces them to reflect on their own situation.

Shifts Focus to Actionable Data

When you ask people how’s it working, you often get one opinion or interpretation of the situation. That’s a fine starting point, since at least they are thinking about and interpreting the situation. However, people have a tendency to interpret based on their own assumptions or biases. They may not have actually collected any actionable data that would be helpful to validate or refute their assumptions.

For example, I recently had a discussion with a senior manager who was explaining how he is using agile development in conjunction with fixed-priced contracts with his sub-contractors. He provided a very detailed description of his approach and then asked what I thought.

I asked, “So how’s that working for you?” His initial response of “OK, I guess” seemed a bit superficial given they had completed more than 10 agile development efforts using this approach.

So, I asked if he had ever requested an accounting report of the actual amounts spent on each of the fixed-price contracts. He had not. I have personally never seen a fixed-price contact where the actual amount paid by the end of the contract was the same as the amount that was originally agreed to. I am sure such examples exist, but I haven’t seen them. Since a company can rarely specify in sufficient detail on the first day what it wants, the sub-contractor will make much of its profit on the overage charges when the 25 pages of change-control language in Appendix A of the contract get invoked when the company requests changes.

The manager did request a report from accounting. And the next day, when we had the actual data in hand, the report showed all of the projects cost more than the originally negotiated prices. At that point the manager didn’t need to know my opinion on what I thought about his approach, he had data to make up his own mind.

Forces Intellectual Honesty

Finally, asking how’s it working forces intellectual honesty. Once you introspect on your own situation and collect actionable data, you reach a, perhaps uncomfortable, moment of truth. You are forced to decide whether you accept what you have learned or not.

Let me provide an example. A few years ago, I was meeting with a senior management team at a division of a large company ($150m/year budget). We were having a discussion about detailed planning and budgeting for the upcoming year. This team had years of experience performing very detailed upfront planning and budgeting prior to the beginning of the next fiscal year.

Senior management accepted that the development teams would use agile, but they still wanted to continue with their familiar heavy upfront planning and budgeting approach. As you might suspect, I asked, “How’s that working for you?” I followed that question with another more pointed question: “You have been doing this form of planning and budgeting for years. When you look at the data of how well it’s worked, what do you conclude? In other words, has it ever worked out that the effort you invested in those detailed upfront plans and budgets has been justified? Or did you end up having to constantly update your plans and budgets when reality deviated from your initial guesses?”

At that moment there was a bit of a (dramatic) pause, and then everyone in the room just busted out laughing. They realized that of course it had never worked out well for them. This was the moment of intellectual honesty. Up till this moment, the idea of doing things like they had in the past was not only on the table, but presumed to be only way forward.

I’m pleased to say the question caught on with at least one person at this particular client. Nowadays, whenever one of the general manager’s subordinates pushes an old agenda, he responds with, “Yeah, and how well has that ever worked out for us in the past?”


When someone is explaining their situation and either asking you for your opinion or you feel compelled to offer them your opinion, I suggest you first consider asking the question, “How’s that working for you?” I have found that this one simple question is one of the most powerful tools in my toolbox for inviting a deeper conversation, forcing introspection, shifting the focus to actionable data, and focusing on intellectual honesty.