Among the most common issues that Product Managers face — particularly those in smaller companies or in companies where Product Management as a discipline is a new thing — is the seemingly random collection of features, functionality, plans, “strategies”, market segments, and really everything that surrounds the role.  Part and parcel of being a good Product Manager is identifying these situations and attempting to get a diverse set of stakeholders focused on a single goal — for at least a brief time.  It’s literally impossible to deliver a good, solid product when everyone and their brother has the ability to derail or randomize the direction that product should take.

The best tool that we have to combat this is simple – question everything.  Ask for specifics, ask for data, ask for testing results — and be willing and able to come up with your own answers when others ask for yours in return.  While it certainly won’t make you the most popular person in the company, Product Management is not a popularity contest — it’s a role whose job is to deliver the best and most compelling solutions to market problems that your customers will be willing to pay for.

Know WHAT Tough Questions to Ask

In order to ask these questions, though, you really need to know what kinds of questions you should be asking.  Nearly all of these questions are relatively easy to decide upon — you ask questions that focus the discussion on the customer and not the stakeholder.  You ask questions about data and not about feelings.  You ask questions that have direct answers, that tighten the focus of the issue at hand, and that “force” the answerer to take a solid stand.  Some of these questions might be:

• How many customers have we vetted this direction with?
• How many users have we tested this new interface with?
• Where does the data from these market size estimates come from?
• Which of these ten ideas is the most important and why?
• Is this strategy the best deployment of our limited resources at this time?

The point of all of these questions is to obtain data upon which the subject is based — or, more often, to uncover and force people to acknowledge that they don’t have any data upon which they have based their conclusions.  If you get the data, you can now analyze it; if you can get an admission that there is no data, then you can collect data to test the hypothesis.

Know HOW to Ask Tough Questions

Nobody likes to be challenged — whether they are developers, managers, directors, account managers, or your CEO.  So the way that you ask these questions is of the utmost importance — you need to understand the situation and the people involved, and you need to ask the question in a way that does not question or attack the integrity of the person you’re talking to, but rather in a way that focuses on the data and the customer.  There are very few people who won’t be willing to engage on a carefully-worded question that points to information or to the customer — doing so falls into the realm of being “disagreeable” all too easily.

Obviously,  you need to know the personalities of the people with whom you’re working, and you’ll need to tailor your questions appropriately.  There may be some people who feel more easily threatened by others, or people who believe that their opinions truly are representative of the market, no matter what the “data” says (or, sometimes, what the customers themselves are saying).  In those situations, you need to work indirectly and through other stakeholders to build pressure — so that it’s not you putting your head on a chopping block unnecessarily.

Know WHEN to Ask Tough Questions

Almost as important as knowing what to ask and how to ask it, is knowing when to ask them.  It is almost never a good idea to ask these kinds of hard, challenging questions in a meeting — especially a meeting that involves a combination of people from varying strata throughout the company.  You should approach these discussions much like you would a situation where you’re in need of correcting some other behavior — praise in public, punish in private.  The ideal context for asking these kinds of questions is to be proactive in discussing the subjects with the people involved — you need to get to them before they’ve put anything on the line for their opinions.

A good PM should have some kind of standing, regular 1:1 meetings with their primary stakeholders, and it’s just those kinds of meetings where these conversations should happen.  They should never be a surprise; they should never come across as a challenge to authority; they should just be a part of doing business on a daily, weekly, or monthly basis.  The more “normal” these questions become, the more part of the daily practice it will be to have the data amongst those who actually care.