Ask: Getting the Right People to Think about the Right Questions

The IWIK process begins as soon as you're asked to tackle an issue that requires conducting analysis, drawing conclusions, and making recommendations.

Before even considering the potential journey to the solution, ask yourself, your colleagues, or your client, who the key stakeholders are. Make a list of the individuals who have a role in implementing any decisions or recommendations you make. Who will care about its success and failure? Use this information to create a stakeholder map, which might look like an organogram, and then whittle this map down to the most important people. Make a shortlist of people who will have the most prominent role in execution and be most impacted by the outcome. Your chosen group should be as diverse as possible, with individuals of different seniority levels and with different tenures. Ideally, they should be from different backgrounds, too. Once you're confident with the group, and depending on your organizational culture, you may consider sending each person an email to request 20 minutes of their time to determine three initial things:

1. The essential questions that they would wish to have answered to move forward with the project confidently.
2. A shortlist of success or outcome metrics that matter to them.
3. Any unknowns that they are curious to explore and that are related to the issue at hand.

This inquiry is all about them—their problems, their questions, their business, and their success.

The goal of the initial communication is to kick‐start the thinking process, to prime the brain pump, so to speak. You're not overwhelming them with sticky notes, whiteboards, or breakout sessions; you're just asking them to start considering and contemplating. As a result, by the time you meet in person or virtually for your session, each participant should be in the right mindset to think creatively.

Brainstorm: Optimizing the Discovery of Information

In a fast‐moving world, you need to gather information and think through a range of solutions. This has often been done by brainstorming. The term brainstorming was coined in 1953 by advertising executive Alex Osborn, who describes it in his book Applied Imagination. Osborn discusses the power of creative imagination “as the basic tool in the acquisition of knowledge.” For knowledge, Osborn reasons, “becomes more usable when imaginatively synthesized and dynamically extended.”⁴ He's spot‐on, yet few leaders take the time to build a culture to tap into this basic tool of imagination, and the typical brainstorming process today falls far from Osborn's ideal of keen synthesis and dynamic extension.

In today's reality, brainstorming is often a massive problem for time‐starved teams. In fact, when we hear the term brainstorming we usually think of colored sticky notes, long days of meetings, flip charts, whiteboards, random ideas, and loud participants dominating smart ones. These sessions are often hard to organize, challenging to lead, inefficient, and ineffective. The results are often a series of ideas that no one knows how to evaluate in a useful way. Virtual meetings add another layer of complexity, amplifying many of these problems.

IWIK is designed to eliminate these issues. IWIK sessions can be conducted as a group discussion; however, based on our extensive experience, we believe that the most productive IWIK sessions tend to be one‐on‐one or in small groups of no larger than three. To optimize the value of IWIK, you should plan to conduct successive rounds of sessions (see Figure 2.1) with various stakeholders. By its very nature, the goal of the exercise is to expose knowledge gaps, and it is essential, as a leader, to understand and appreciate that some people are more comfortable than others highlighting what they don't know and acknowledging the limits of their competencies. Small group discussions have the advantage of unlocking conversations that may not happen in other group settings because of fear or inhibition.

A more intimate group is also likely to be sensitive to various personality types and communication styles. Introverts particularly might not feel comfortable contributing in larger groups. Finally—on an entirely practical level—smaller group meetings might be shorter in duration and easier to schedule. Fewer calendars have to be coordinated, and the time spent with a small number of stakeholders may also deepen critical professional relationships in a unique way.

Capture: Leading IWIK Discussions

Leading an IWIK session is simple, deceptively simple. Your role is that of a scribe. When you ask your colleagues or clients “What do you wish you knew?”, you're extending an invitation to them to think expansively without concern for existing data, time, resources, headwinds, budgets, or guard rails.

When you first do this, you might be met with blank stares and stony silence. But don't be taken aback. This reaction may occur because you have just opened a new portal to the imagination, and that takes some getting used to. Rationally, we're all aware of the power of imagination. It's just that the business world in which many of us operate has conditioned us to think within parameters and constraints. That environment has wired us to refrain from thinking creatively, or at least to be extremely cautious when doing so. IWIK can change that and help us become comfortable with thinking differently, challenging the status quo, and talking as honestly and openly as possible about the things we don't know but wish we did.

An interesting dynamic occurs after you pose the IWIK question: The mode slowly shifts from a quiet, awkward silence to one of high energy. Once the questions start flowing, your colleagues, liberated from the pressure to know and have answers, may actually feel unable to stop. Not unlike a series of dominos, once the first few IWIK statements begin to fall, the rest follow.

What's important to bear in mind at this stage is not to answer any of the questions that come up. The competitive environment nurtured by the world of work might create the temptation to do so, but it's crucial to resist: dedicate this phase to generating the IWIK statements rather than getting distracted by what the answers might be.

In the same vein, avoid editorializing on questions in real time. Refrain from commenting on the question or sharing what you have learned so far or what you expect. Commenting on a question can interfere with the openness or flow of the process. For example, if you respond to a colleague's IWIK statement by saying “Three other people in operations asked the same question you did. I am surprised you are raising similar issues in marketing.” you might unintentionally sidetrack your colleague's train of thought.

Particularly if you host several IWIK sessions, the IWIKs that arise will no doubt begin to duplicate. This isn't a bad thing. In fact, you can glean insights from these repetitions that might prove invaluable to your understanding of the problems at hand. In itself, that is a critical data point that will shape your data discovery step. Record every question in every session, even if it is a duplicate. During the process, resist the urge to share that you've heard something before, or the inverse, that you haven't. Be a neutral party. You will have plenty of opportunities to add your insights and synthesize your interpretation later on.

The key to effectively implementing IWIK is to make sure the process is not rushed and that all relevant stakeholders have the opportunity to provide their full input, including the things they know and the things they don't know, as well as the things they need to know and the things they don't need to know.

The output of an IWIK session will be a series of statements or questions highlighting what people want to know. Leading multiple sessions may result in numerous IWIKs being put forward, and while you might fear information overload, don't worry. At this stage, overload is perfectly fine. The IWIK process is designed to help us navigate this risk too. In the next part of IWIK, you will dedicate time and effort to thoroughly organizing all the captured information, so you won't feel like you're swimming in a disorganized swamp of data points. As you review the questions, they will reveal patterns around the essential needs as well as potential duplication of efforts across team members, conflicting requirements, and clarity on the outcomes and biases.

Once you have captured the IWIKs, it is time to categorize them.

Deliberate: Ordering, Aggregating, and Synthesizing IWIKs

When you've collected all the IWIKs, the questions will vastly outnumber the answers, meaning that your job now is to create order and aggregate. You may be sitting looking at 10, 20, 50, or more statements generated from your IWIK sessions. That might feel overwhelming, but you're actually on track.

You've successfully broken down the initial situation into its components. The goal of organizing the IWIKs is to identify patterns in the requests and look for duplicates and outliers. You're on the path to understanding the root of the issue, and this, in turn, will inform the essential data you need, guide the specific analysis required, and focus your efforts on what matters most to your stakeholders, leading to faster, more confident decisions.

Consider the following steps optional if you have a shortlist of statements, for example, fewer than 12. Depending on your knowledge of the underlying issue and mastery of existing data, you can quickly analyze the IWIK statements without formally applying steps 1–5. Like any new skill, the more you use IWIK, the higher your comfort level will be and the faster you'll be able to process things. Mastering IWIK is analogous to learning to drive: at first, you study the driver's manual and are conscious of every step. Over time, you become unconsciously competent; you promptly assess situations on the road and react quickly, with confidence.

Step 1. Create an inventory. Build a simple table (see Table 2.1). Consider using a spreadsheet (e.g., Google Sheets, Microsoft Excel, Apple Numbers) so that you can quickly sort and filter the list. A Microsoft Word document will also work, but the manipulation of the statements might prove harder.

Save this file as IWIK_Master_[project name]. Then open it and save a second copy under a different name, as you will be doing a fair bit of manipulation of the IWIKs. If you accidentally delete a statement, you will have the master file for reference. Alternatively, if you are using a spreadsheet, you can simply duplicate the tab as your backup.

Enter all of the IWIKs you captured into the table along with the person or team who provided each. At this stage in the process, do not dismiss any IWIKs; any single IWIK could point you to an essential piece of analysis or data. Enter all of them. Number them 1, 2, 3, and so on, in column 1, so you can quickly reference any statement later.

Step 2. Code the statements. As you read the statements, assign a letter, for example, A, B, C, in column 2. If you come across a similar statement, assign the same letter. In column 5, enter “Yes” or “No” if you already have the data or can easily find it to satisfy the statement. In column 6, assign an M or an N, denoting must‐haves or nice‐to‐haves. Don't worry about getting it perfect. This file is for your use only. You will have the opportunity to revise.

Step 3. Sort. Begin sorting the IWIKS by column 2. Look for patterns on how many statements have the same letter, which points to a significant knowledge gap and helps establish specific areas to explore. Next, sort by column 6, which will uncover priority needs.

Step 4. Analyze. A helpful tool to make sense of the IWIKs—the raw material you've collected—is to create a simple two‐by‐two matrix of four buckets. The x‐axis denotes the current information, while the y‐axis is divided into what you currently know and what you do not need to know to make the best possible decision. We call this your IWIK Knowledge Matrix™ (see Figure 2.2).

This mapping of the IWIK statements to each bucket helps you frame the problem and will serve as a guide in your data discovery (see Figure 2.3). There's no right or wrong number of questions to have in each quadrant.

Step 5: Assess data needs. The matrix regulates the firehose of information as it paints a picture of your data needs. The bottom half reveals where you are collecting data that is not critical for the current decision you are tackling, so you can stop gathering or analyzing unnecessary data. The top is where you want to focus, as these are the essential questions your stakeholders identified as the must‐have IWIKs to move forward.

At this point, you are in a very good place as you have deconstructed the initial problem into its core elements. You can easily translate this map into a data discovery plan (see Table 2.2). By taking the questions plotted in the upper right quadrant, you can now assess the time, cost, and resources needed to answer this question. The Knowledge Matrix becomes a practical tool to prioritize work for your team: by guiding data discovery efforts, it ensures that your team is working on what matters.