Strategy, Facilitation and Art of Asking Questions

In my last post, I talked about some visual thinking techniques strategists should add to their facilitation toolbox. This post will dive deep into the questions you can ask to ensure teams make good decisions and paddle in the same direction.

TL;DR

• Asking questions is a powerful tool to uncover misalignments and misunderstandings and raise awareness of the need for facilitation.
• I’ve been trying to develop a set of questions that I can always go back to for driving product vision forward; in this article, I’ve broken them down into questions that help Adopt varying mental states, Develop process awareness, Strategic Alignment, Problem Framing.
• Suppose your team has not taken a complete strategic thinking approach to product development. In that case, you can ask a few questions to trigger the critical strategy definitions regarding what’s worth doing, what we are creating, and what value it delivers.
• The pushback I’ve got from many designers is that their stakeholders might not have the answers even if they were to ask the strategy questions above. In these situations, taking cues from the Lean UX playbook and capturing hypotheses is very useful.
• To understand the risk and uncertainty of ideas, all you need to ask is what things need to be true for this idea to work? This will allow you to identify all four hypotheses underlying a business idea: desirability, feasibility, viability, and adaptability.
• I find it incredibly important that designers need to ask good questions that foster divergent thinking, explore multiple solutions, and — probably the most critical — help teams converge and align on the direction they should go.
• I’ve seen many teams trying to start a conversation around features with a problem statement. The problem with problem statements (pun intended) that I’ve found is that there are many thinking traps and decision biases that stakeholders and team members might not even be aware of.
• It’s essential to question the things that everyone else takes for granted, such as rules that cannot be broken or fixed parameters that can never be challenged, like: Are we asking the right questions? Why do we need to solve this problem? Why do we do thinks this way at all? How can we restate the problem?
• There is no point in asking questions if you’re not ready, willing, or able to listen: listening lets you understand someone — or a situation — on several levels.
• The hardest part of getting better at asking questions is to do this habitually. The behavior has to become routine to have a meaningful and long-lasting impact. It should be part of the way we do our jobs. It should be part of how we do our jobs and incorporated into our everyday interactions with others.

Shared Understanding and Asking Questions

Earlier in this series, I mentioned I’ve found that — more often than not — it is not for the lack of ideas that teams cannot innovate, but because of all the friction or drag created by not having a shared vision and understanding of what the problems they are trying to solve.

To make sure I’m understood: it doesn’t matter at that point if the team lacks a vision or the vision is just poorly communicated; the result is the same: the team will lack engagement and slowly drift apart.

Shared understanding is the collective knowledge of the team that builds over time as the team works together. It’s a rich understanding of the space, the product, and the customers.

“Creating Shared Understanding” in Lean UX: Applying lean principles to improve userexperience, Gothelf, J., & Seiden, J. (2013)

Teams that attain a shared understanding are far more likely to get a great design than those teams who fail to develop a common perception of the project’s goals and outcome (Jared Spool, “Attaining a Collaborative Shared Understanding” in Govella, A., Collaborative Product Design, 2019).

When teams share an understanding, everyone knows what they’re working on, why it’s important, and what the outcome will look like.

Govella, A., Collaborative Product Design (2019)

It’s straightforward to verify if the team lacks understanding of the problem it is trying to solve. Just ask fundamental questions in your next meeting, like “what is the problem we are trying to solve”? “And for whom”?” “why are we working on this”?

Suppose you get different answers from critical stakeholders. In that case, it is probably a good indication that you should jump in and help facilitate the discussion that will help the team to align: asking questions is a powerful tool to uncover misalignments and misunderstandings and raise the awareness of the need for facilitation.

Perhaps nothing is more important to exploration and discovery than the art of asking good questions. Questions are fire-starters: they ignite people’s passions and energy; they create heat; and they illuminate things that were previously obscure.

Gray, D., Brown, S., Macanufo, J., “Core Gamestorming Skills” in Gamestorming (2010)

Questions are powerful. And the words we choose for them are critical, because changing just one word can change your answers (Shapiro, S., Invisible solutions: 25 Lenses that reframe and help solve difficult business problems, 2020):

• Questions impact your thought process: Asking the right question in the right way is the surest way to accelerate finding better solutions. Sometimes a tiny change can have a significant impact on the way you find the problem.
• Questions impact your emotional state: they impact not just the solution and the thought process, but also how we feel. Unfortunately, we ten to ask questions that are not effective or impactful.

When people frame their strategic exploration as questions rather than as concerns or problems, a conversation begins where everyone can learn something new together, rather than having the normal stale debates over issues

Brown, J., & Isaacs, D., The world cafe: Shaping our futures through conversations that matter (2005)

A power question (Brown, J., & Isaacs, D., The world cafe: Shaping our futures through conversations that matter, 2005):

• Is thought provoking
• Challenges assumptions
• Generates energy
• Focuses inquiry and reflection
• Touches a deeper meaning
• Evokes related questions

Asking Questions the Mindset of the Facilitator

After many workshops (and conversations on Clubhouse), I’ve been trying to develop a set of questions that I can always rely on to drive our vision forward. I’ve decided to breakdown these questions to match the mindset of the facilitator — some of them we’ve covered before in Lewrick, M., Link, P., & Leifer, L., The design thinking playbook, 2018:

• Adopting varying mental states. As the situation requires, we combine different approaches with design thinking, data analytics, system thinking, game storming, and lean start-up
• Developing process awareness. We know where we stand in the design thinking and/or other facilitation processes and develop a strong sense of when is the right time to change the mindset (e.g.: from divergent to convergent).

I’ll add some questions for bonus also:

• Questions for Strategic Alignment: It is crucial that designers engage with their business stakeholders to understand what objectives and unique positions they want their products to assume in the industry, and the choices that are making in order to achieve such objectives and positions.
• Questions for Problem Framing: It’s important to questions the things that everyone else takes for granted.

What follow are sets of questions that will help you cover the different aspects of walking team through the strategy journey.

Asking Questions and Process Awareness

In my experience, the most significant disconnect between the work designers need to do, and the mindset of every other team member in a team is usually about how quickly we tend — when not facilitated — to jump to solutions instead of contemplating and exploring the problem space a little longer.

I think designers should facilitate the discussions and help others raise awareness around the creative and problem-solving process instead of complaining that everyone else is jumping to solutions too quickly.

From that perspective, I find it incredibly important that designers need to ask good questions that foster divergent thinking, explore multiple solutions, and — probably the most critical — help teams converge and align on the direction they should go (Gray, D., Brown, S., & Macanufo, J., “What is a Game?” in Gamestorming, 2010).

Following a pattern that leads with divergent thinking and concludes with convergent thinking helps you manage those tangents. Tangents can feel frustrating, but good tangents are one of the best things that come out of meetings. Good, novel ideas come from diverse opinions and experience. Going off on tangents is a way to get to those ideas. They won’t all be great ideas, but a few of them could be better than what you might come up with working alone (Hoffman, K. M. Meeting Design: For Managers, Makers, and Everyone. 2018).

Knowing when the team should be diverging, when they should be exploring, and when they should closing will help ensure they get the best out of their collective brainstorming and the power of multiple perspectives to keep the team engaged.

You should steer a conversation by asking the right kinds of questions, based on the problem you’re trying to solve. In some cases, you’ll want to expand your view of the problem, rather than keeping it narrowly focused (Pohlmann, T., & Thomas, N. M., Relearning the art of asking questions, 2015):

• Clarifying questions help us better understand what has been said. In many conversations, people speak past one another. Asking clarifying questions can help uncover the real intent behind what is said. These help us understand each other better and lead us toward relevant follow-up questions. “Can you tell me more?” and “Why do you say so?” both fall into this category. People often don’t ask these questions, because they tend to make assumptions and complete any missing parts themselves.
• Adjoining questions are used to explore related aspects of the problem that are ignored in the conversation. Questions such as, “How would this concept apply in a different context?” or “What are the related uses of this technology?” fall into this category. For example, asking “How would these insights apply in Canada?” during a discussion on customer life-time value in the U.S. can open a useful discussion on behavioral differences between customers in the U.S. and Canada. Our laser-like focus on immediate tasks often inhibits our asking more of these exploratory questions, but taking time to ask them can help us gain a broader understanding of something.
• Funneling questions are used to dive deeper. We ask these to understand how an answer was derived, to challenge assumptions, and to understand the root causes of problems. Examples include: “How did you do the analysis?” and “Why did you not include this step?” Funneling can naturally follow the design of an organization and its offerings, such as, “Can we take this analysis of outdoor products and drive it down to a certain brand of lawn furniture?” Most analytical teams – especially those embedded in business operations – do an excellent job of using these questions.
• Elevating questions raise broader issues and highlight the bigger picture. They help you zoom out. Being too immersed in an immediate problem makes it harder to see the overall context behind it. So you can ask, “Taking a step back, what are the larger issues?” or “Are we even addressing the right question?” For example, a discussion on issues like margin decline and decreasing customer satisfaction could turn into a broader discussion of corporate strategy with an elevating question: “Instead of talking about these issues separately, what are the larger trends we should be concerned about? How do they all tie together?” These questions take us to a higher playing field where we can better see connections between individual problems.

Divergent Thinking and Increasing Abstraction

When your problem statement is overly specific or implies a particular solution or area of expertise, increasing abstraction will help you expand your thinking to increase the range of possibilities.

While facilitating divergent thinking, remind people to be open-minded. Divergent activities include making lists, having open-ended discussions, and collecting perspectives. During divergent thinking, it’s the facilitator’s job to remind the group to suspend judgment. It’s OK to allow discomfort in the group and have an unresolved conflict. Ideas may contradict each other, but the more ideas, the better. Get the obvious ideas out of the way and move on to the ones that require a little more effort (Hoffman, K. M. Meeting Design: For Managers, Makers, and Everyone. 2018).

The idea behind divergent thinking is to generate ideas and options, provoke thought and reveal possibilities, and jump-start the brain. Good opening questions open doors to new ways of examining a problem statement.

Gray, D., Brown, S., Macanufo, J., “What is a Game?” in Gamestorming (2010)

Here are a few questions to trigger the discussion that will lead to an increased level of abstraction (Shapiro, S., Invisible solutions: 25 Lenses that reframe and help solve difficult business problems, 2020):

• Analogy: what is this like? Who else has solved a problem like this?
• Result: what does this make possible? What is the desired outcome?
• Concern Reframe: how can we take a progress-blocking statement and convert it into a questions that starts with “How can we…?”
• Stretch: Are our problem statement criteria stretched enough? Are we shooting for a high enough goal?
• Hypernym: How can we replace a word in the problem statement with a less specific instance of the one originally chosen?

Convergent Thinking and Reducing Abstraction

At some point, the facilitator should turn the boat around and switch the focus to convergence. The facilitator should help the group decide if one tangent is better than another. Where divergent thinking is about being OK with disagreement, convergent thinking is about eliminating excess, or the least likely stuff to succeed. Once the corner has been turned, the facilitator helps the group summarize the essence of each approach to decide what’s worth keeping and how to act upon it (Hoffman, K. M. Meeting Design: For Managers, Makers, and Everyone. 2018).

When your problem statement is overly large, broad, or abstract, reducing abstraction (or convergent thinking) will help you bring you down to earth (Shapiro, S., Invisible solutions: 25 Lenses that reframe and help solve difficult business problems, 2020).

Closing questions serve the opposite function from opening questions: when you’re opening, you want to create as much divergence and variation as possible. When you’re closing, you want to focus on convergence and selection. Your goal is to move towards commitment, decisions, and action.

Gray, D., Brown, S., Macanufo, J., “What is a Game?” in Gamestorming (2010)

Here are a few approaches geared toward making questions more more specific when they are too broad (Shapiro, S., Invisible solutions: 25 Lenses that reframe and help solve difficult business problems, 2020):

• Leverage: what is the one factor that will have the greatest impact? What give us the greatest leverage in solving this problem?
• Deconstruct: what are the part or components of this? What are the steps of the process? What are the different segments?
• Reduce: how might lowering the goals and expectations give us a better result or create new opportunities for growth? How can implication increase usability and accessibility?
• Eliminate: how can this be eliminated? Instead of adding features, what features can you remove?
• Hyponym: is there a more specific instance of a word that can replace the one originally chosen?

Asking Questions for Strategic Alignment

As we discussed earlier, “any product that makes into the the world it’s actually the outcome of a set of dozens, hundreds or thousands of decisions along the way. Each decision building upon each other, informing and influencing all aspects of the user experience”. (“Elements fo User Experience: User-Centered Design for the Web and Beyond“, Garrett, 2010).

Strategy is a set of choices about winning that uniquely positions the firm in its industry so as to create sustainable advantage and superior value relative to the competition.

“How Strategy Really Works” in Playing to Win: How Strategy Really Works (Lafley, A.G., Martin, R. L., 2013)

Designers must engage with their business stakeholders to understand what objectives and unique positions they want their products to assume in the industry and the choices made to achieve such goals and positions.

Asking the questions above will help you confirm strategic alignment, allowing designers to understand better — and influence — the business decisions that help create such an advantage and superior value to the competition.

The design team also needs to assess the extent to which a shared vision drives the challenge at hand by asking three questions (Calabretta et al. “Designing Transitions: Pivoting Complex Innovation” in Strategic Design: 8 Essential Practices Every Strategic Designer Must Master. 2016):

• Is there a project vision? Does the company have a clear view of the project direction, and where it fits into the raison d’être (the “why”) of the company? How exactly will the project help the company fulfill it’s why? A satisfactory answer to this question should emerge during the early stages of a strategic project, when the brief is formulated. Lack of clear-cut answer to these questions usually signals the absence of a strong, cohesive project vision.
• Is the project a good fit with the wider goals of the organization? Sometimes the project vision does not align with the KPIs or primary goals that the organization has expressed elsewhere. This usually happens – for example – when a trend emerges and organization may act impulsively because they are afraid to miss out on what they see as an opportunity for growth.
• Is the vision shared across the company? If there is a clear project vision, is there widespread awareness and alignment within the company? Can various department move in the same direction during project setup and implementation?

If your team has not embarked on a full strategic thinking approach to product development, you can ask few questions to trigger the important strategy definitions with regards to what’s worth doing, what are we creating, and what value it delivers (Natoli, J., Think first, 2015):

What’s worth doing

After you’ve got a hand with what the business needs, along with understanding what users need, we should help the team answer the questions about what’s actually worth our time and effort? What’s worth the organization’s investment in the project? What’s worth our time and investment in the project?

The answers to those questions are determined by figuring out what the tradeoffs are between the product’s importance and its feasibility/viability (Natoli, J., Think first, 2015).

What are we creating

Part of the job of a design strategist is to make sure that everyone at the table is in agreement. You want a shared understanding of the project goals and what needs to be designed and built in order to meet those goals. And you want to make sure that your discussions address the why in the addition of the what (Natoli, J., Think first, 2015).

Taking the time to dig in deep during the strategy phase will pay dividends over and over as the project progresses. You will find that subsequent phases will run much more smoothly.

What value does it deliver?

That — as you imagine — is a pretty big question. The good news is that there are a series smaller questions that can help you answer it Natoli, J., Think first, 2015):

• What is the target audience?
• What experiences are compelling for these people?
• How is our offering going to be different from the competitors?

Solve for the greatest impact

Identifying good leverage points can kick-start the problem-solving process. It allows you to focus on what will return the greatest value, with the least amount of investment. Then, after you solve for the first leverage point, you can work on the next. To identify leverage point, ask (Shapiro, S., Invisible solutions: 25 Lenses that reframe and help solve difficult business problems, 2020):

• What is the one factor that will have the greatest impact?
• What gives us the greatest leverage in solving this challenge?
• What’s the most important factor in driving change?
• If we could only solve one aspect of this problem, what would give us the greatest result?

What are our priorities?

As a design manager, I’ve always found that — while defining and shaping the Product Design vision to ensure cohesive product narratives through sound strategy and design principles — the way priorities are defined can potentially create a disconnect from vision, especially when tough choices around scope needs to be made. We must facilitate discussions around priorities so that the hard choices that need to be made are taken into account, not just feasibility but also viability and desirability.

The goal with prioritization is to determine what to complete next in order to get maximum value in the shortest amount of time and to avoid multi-tasking due to competing priorities (DeGrandis, D., Making work visible: Exposing time theft to optimize workflow, 2017).

Priorities Make Things Happen

Berkun, S., Making things happen: Mastering project management (2008)

It’s essential to set priorities and remove distractions so that people can get on with providing service to customers, thus increasing profits and the value of the business (Kourdi, J., Business Strategy: A guide to effective decision-making, 2015).

While priorities can make things happen, we need to prioritize things that are important by focusing on value.

The build trap is when organizations become stuck measuring their success by outputs rather than outcomes. It’s when they focus more on shipping and developing features rather than on the actual value of those things.

Perri, M., Escaping the build trap (2019)

There are a few things you should ask yourself and/or the team when we keep coming revisiting and renegotiating the scope of work (DeGrandis, D., Making work visible: Exposing time theft to optimize workflow, 2017):

• What is your prioritisation policy and how is it visualised? How does each and every item of work that has prioritised helps get us closer to our vision and achieve our goals?
• How will you signal when work has been prioritised and is ready to be worked on? In other words — where is your line of commitment? How do people know which work to pull?
• How will we visually distinguish between higher priorities and lower priority work?

Asking Questions and Capturing Assumptions

The pushback I’ve got from many designers is that — even if they were to ask the strategy questions above (see Asking Questions for Strategic Alignment) — their stakeholders might not have the answers. In these situations, taking cues from the Lean UX playbook and capturing hypotheses is very useful.

Many companies try to deal with complexity with analytical firepower and sophisticated mathematics. That is unfortunate since the essential elements of creating a hypothesis can typically be communicated through simple pencil-and-paper sketches (Govindarajan, V., & Trimble, C., The other side of innovation: Solving the execution challenge, 2010.)

The key to dealing with complexity is to focus on having good conversations about assumptions.

Break Down the Hypothesis in The other side of innovation: Solving the execution challenge, Govindarajan, V., & Trimble, C., (2010)

The idea is that we write our ideas, not as requirements, but as our best guesses for how to deliver value and with clear success criteria to tell us whether our idea was valuable and we delivered it in a compelling way (Gothelf, J., & Seiden, J., Lean UX, 2013):

We believe
[this outcome] will be achieved if
[these users] attain [a benefit]
with [this solution/feature/idea].

Gothelf, J., & Seiden, J., “Hypothesis Template” in Lean UX, (2013)

If you only have one hypothesis to test it’s clear where to spend the time you have to do discovery work. If you have many hypotheses, how do you decide where your precious discovery hours should be spent? Which hypotheses should be tested? Which ones should be de-prioritised or just thrown away? To help answer this question, Jeff Gothelf put together the Hypothesis Prioritisation Canvas (Gothelf, J., The hypothesis prioritization canvas, 2019):

To understand the risk and uncertainty of your idea, you need to ask: “What are all the things that need to be true for this idea to work?” This will allow you to identify all four types of hypotheses underlying a business idea: desirability, feasibility, viability, and adaptability (Bland, D. J., & Osterwalder, A., Testing business ideas, 2020):

• Desirability: Does the market want this idea?
• Feasibility: Can we deliver at scale?
• Viability: Is the idea profitable enough?
• Adaptability: Can the idea survive and adapt in a changing environment?

As we ask these questions, though, we need to be open to all possibilities, not just confirm our assumptions.

Our questions can be powerful tools for learning, but only if they challenge our assumptions rather than confirm our beliefs

Shapiro, S., Invisible solutions: 25 Lenses that reframe and help solve difficult business problems (2020).

When your team needs a “reality check,” identify your assumptions and the best ways to address them (IBM Enterprise Design Thinking, Assumptions and Questions, 2018).

1. Collect assumptions: Diverge, with each team member writing one assumption or question per sticky note. Withhold judgement or discussion until later.
2. Set up the activity: Draw a two-by-two grid with High-risk on the top, Low-risk on the bottom, Certain on the left, and Uncertain on the right.
3. Identify high-risk uncertainties: Evaluate each idea quickly and individually. Roughly plot them on the grid where they make most sense. Once many items are on the grid, begin to discuss with your teammates and re-position them in relation to each other.
4. Build an action plan: Pull high-risk and uncertain items from the upper-right quadrant into a new space. For each item, diverge on many different ways to validate or invalidate these assumptions and questions. Is there someone you can talk to directly to get an answer? Could you validate an assumption through direct observation? Could you build a prototype to test a hypothesis?

A successful project is not deemed successful because it is delivered accordant to a plan, but because it stood the test of reality.

“Walk the walk” in The decision maker’s playbook. Mueller, S., & Dhar, J. (2019)

Another variation of the pushback I’ve got from many designers is that — even if they were to ask the strategy questions above (see Asking Questions for Strategic Alignment) — their stakeholders might have a hard time framing conversations and keeping a clear state of mind to differentiate fact from assumptions.

In these situations, visual thinking canvases and other facilitation techniques can help them (and you) stay focused.

Asking Questions and the Fact Finder

That’s when you need to keep going down the rabbit hole and talk about thinking traps and problem framing tools. Check some thinking traps below (Mastrogiacomo, S., Osterwalder, A., Smith, A., & Papadakos, T., High-impact tools for teams, 2021):

• Unclear facts or experiences: Absence of key information in the description.
• Generalizations: When we turn a particular case into a universal law.
• Assumptions: Creative interpretations of an experience or situation.
• Limitations: Imaginary rules and obligations inferred from the situation.
• Judgements: Individual evaluations of a thing, a situation or a person

By asking clarification questions that help everyone get back to the original facts and experiences hidden behind assumptions, judgements, rules and so on (Mastrogiacomo, S., Osterwalder, A., Smith, A., & Papadakos, T., High-impact tools for teams, 2021):

What’s important to understand is that testing rarely means just building a smaller version of what you want to sell. It’s not about building, nor selling something. It’s about testing the most important assumptions, to show this idea could work. And that does not necessarily require building anything for a very long time. You need to first prove that there’s a market, that people have the jobs pains and gains and that they’re willing to pay (Bland, D. J., & Osterwalder, A., Testing business ideas, 2020).

Asking Questions, Problem Framing and Reframing

To bring clarity and shared understanding on what problems we are trying to solve, I’ve seen many organizations try to be more systematic and adopt artifacts like Problem Statements.

Problem statements are widely used by most businesses and organizations to execute process improvement projects. A simple and well-defined problem statement will be used by the project team to understand the problem and work toward developing a solution. It will also provide management with specific insights into the problem so that they can make appropriate project-approving decisions. As such, it is crucial for the problem statement to be clear and unambiguous (Annamalai, Nagappan; Kamaruddin, Shahrul; Azid, Ishak Abdul; Yeoh, TS, 2013).

The problem with problem statements (pun intended) that I’ve found is that we are unaware of many thinking traps and decision biases while writing such problem statements. Don’t get me wrong: problem statements are essential! What I’m trying to say is that — if you’re going to write some — be better to get them right! Let’s see how!

Before applying any specific reframing strategies, it’s a good practice to start with a review of the problem statement. Here are some questions that can help you do that (Wedell-Wedellsborg, T.,  What’s Your Problem?, 2020):

• Is the statement true?
• Are there simple self-imposed limitations?
• Is a solution baked into the problem framing?
• Is the problem clear?
• With whom is the problem located?
• Are there strong emotions?
• Are there false trade-offs?

Problem Statements and Decision Biases

As I mentioned, I’ve found many thinking traps (some discussed earlier) and decision biases that stakeholders and team members might not even be aware of while writing problem statements. The most classic is to bake the solution into the problem statement. This has been illustrated well by Marc Rettig:

Design a Vase
Design a better way for young families to enjoy flowers in their home

Rettig, M., (2010) “Design a Vase”, in An evening of conversation about Design, Interaction, Work and Life, May 25th, 2010, IxDA Gathering, 399, Pu DianRoad, Pudong New District, Shanghai, 200122, P.R. China

A couple of ways to avoid such traps is — obviously — beware of such biases (check some below) and keep asking questions.

With regards to biases, here are a few to be aware of (Hammond, et al. The Hidden Traps in Decision Making, 2013):

• The Anchoring Trap lead us to give disproportionate weight to the first information we receive
• The Status-quo Trap biases us towards maitaining the current situation – even when better alternatives exist
• The Sunk-Cost Trap inclines us to make choices in the way that justifies past choices, even when these were mistakes
• The Confirming-Evidence Trap leads us to seek out information supporting an existing predilection and to discount opposing information.
• The Framing Trap occurs when we misstate a problem, undermining the entire decision-making process
• The Overconfidence Trap makes us overestimate the accuracy of our forecasts
• The Prudence Trap leads us to be overcautious when we make estimates about uncertain events.
• The Recallability Trap prompts us to give undue weight to recent, dramatic events

With these biases in mind, you should trigger team discussions before they make any big decision (Kahneman, D., Lovallo, D., & Sibony, O., “The Big Idea: Before You Make That Big Decision” in HBR’s 10 must reads on making smart decisions, 2013):

Questions that decision makers should ask themselves

• Check for the self-interest bias: is there any reason to suspect the team making the recommendation of errors motivated by self-interest. Review with extra-care, especially for overoptimism.
• Check for the affect heuristic: has the team fallen in love with its proposal? Rigorously apply all the quality controls on this checklist.
• Check for groupthink: were there dissenting opinions within the team? Were they explored adequately? Solicit dissenting views, discreetly if necessary.

Questions that decision makers should ask the recommenders

• Check for salience bias: could the diagnosis be overly influenced by an analogy to a memorable success. Ask for more analogies, and rigorously analyse their similarity to the current situation.
• Check for the confirming bias: are credible alternatives included along with the recommendation? Request additional options.
• Check for availability bias: if you had to make this decision again in a year’s time, what information would you want, and can you get more of it now? Use checklists of the data needed for each kind of decision.
• Check for anchoring bias: do you know where the numbers came from? Can there be unsubstantiated number? Extrapolation from history? A motivation to use a certain anchor? Reanchor with figures generate by other models or benchmarks and request for new analysis.
• Check for the halo effect: is the team assuming that a person, organisation, or approach that is successful in one area will be just as successful in another? Eliminate false inferences, and ask the team to seek additional comparable examples.
• Check for the sunk-cost fallacy, endowment effect: are the recommenders overly attached to a history of past decisions? Consider the issue as if you were a new CEO.

Questions that decision makers should ask about the proposal

• Check for the overconfidence, planning fallacy, optimistic biases, competitor neglect: is the base case overly optimistic? Have the team build a case taking an outside view.
• Check for disaster neglect: is the worst case bad enough? Have the team conduct a premortem: imagine that the worst has happened, and develop a story about the causes.
• Check for loss aversion: is the recommendation team overly cautious? Realign incentives to share responsibility for the risk or to remove risk.

Asking Questions and Lateral Thinking

It’s essential to question the things everyone else takes for granted, such as rules that cannot be broken or fixed parameters that can never be challenged. The kinds of questions to explore the problem space from a lateral thinking perspective include (Sloane, P., The leader’s guide to lateral thinking skills, 2017):

• Are we asking the right question?
• Why do we need to solve this problem?
• Why do we think this way at all?
• How can we restate the problem?
• Who would benefit and who would lose if we solve this problem?
• What are the rules of our business and what would happen if we broke those?
• What are we assuming about this situation?
• What would happen if we challenged those assumptions?
• Can we draw a diagram or picture of the problem?
• Can we model the problem?
• How would someone from another planet solve this problem?
• If we had unlimited money and resources how would we solve this problem?
• How would someone in a completely different line of business solve this problem?
• How can we look at this in a different way?

Asking Questions, and Reframing

Sometimes, to solve a hard problem, you have to stop looking for solutions to it. Instead, you must focus on the problem – not just to analyze it but to shift how you frame it.

Reframing is a powerful technique that focuses on diagnosing a given problem – such as “what is preventing us from making progress” or perhaps a problem faced by your customers – and then, crucially, challenging and reframing your initial perception of that problem (Wedell-Wedellsborg, T., What’s Your Problem?, 2020).

You cannot look in a new direction by looking harder at the same direction

De Bono, E., Lateral Thinking: Creativity Step by Step (2015)

Reframing is seeing the current situation from a different perspective, which can be tremendously helpful in solving problems, making decisions, and learning. When people get stuck in a recurring issue in a complex situation or in solving a complex problem, it is rarely because they miss a certain step-by-step procedure to fix things. Instead, it is often because they are stuck in how they see the situation (Wedell-Wedellsborg, T., What’s Your Problem?, 2020)

There are five nested strategies can help you find these alternative framing of the problem (Wedell-Wedellsborg, T., What’s Your Problem?, 2020):

• Look outside the frame. Are there elements we are not considering? Is there anything outside the frame that we are not currently paying attention?
• Rethink the goal. Is there a better goal to pursue?
• Examine bright spots. Have we already solved the problem at least once? Are there positive outliers in the group? Who else deals with this type of problem? Can we broadcast the problem widely?
• Look in the mirror. What is my/our role in creating this problem? Scale the problem down to your level. Get an outside view of yourself.
• Take their perspective. You will get people wrong unless you invest genuine effort in trying to understand them. List the parties and listen to them. Escape your own emotions. Look for reasonable explanations.

Better Decisions, Fewer Regrets

If you’ve been doing any facilitation or coaching for as long as I have, you’ve probably been approached by people over coffee or after a workshop, or after whatever challenging situation they are experiencing, who ask for help in solving problems or to make good decisions that don’t require complicated models, or there is no need for prototypes. These issues usually involve something more at the personal level or interpersonal dynamics.

Communicator, author, and pastor Andy Stanley (founder of Atlanta-based North Point Ministries) have coached many leaders — both as a pastor and organizational change thought leader — and he has devised a simple process for making good decisions based on a straight-forward, common sense set of assumptions (Stanley, A., Better decisions, fewer regrets: 5 Questions to help you determine your next move, 2020):

• Our decisions determine the direction and the quality of our lives
• A response is a decision 
• Your decisions determine the story of your life 
• Decide on a good story 
• Good questions lead to good decisions;
• Good decisions lead to fewer regrets.
• While nobody plans to complicate their life with bad decisions, far too many people don’t plan not to.
• Well-placed, appropriately timed, thought-provoking questions helps us think through our decisions.

Andy Stanley introduces 5 questions that equip you to make better financial, relational, and professional decision. These questions are designed to serve as a decision-making filter for making good decisions.

• The Integrity Question. Am I being honest with myself … really? You may not owe it to anyone else, but you owe it to yourself to be honest why you choose what you choose, why you are deciding what you are deciding. Decide not to lie to yourself or be creative to justify your decisions.
• The Legacy Question. What story do I want to tell? The primary reason we don’t think in terms of story when making decision is that story is later. Decisions are now. We think about later, later. As in later when it’s too late to do anything about it. We don’t think in terms of story because we’re distracted by the pressure and emotions we feel in the moment. Decide on a story you are proud to tell.
• The Conscience Question. Is there a tension that deserves my attention? Sometimes — in fact, more times that we would like to admit — an option we’re considering creates a little tension inside of us. Experts sometimes refer to this phenomenon as a red flag moment, an internal sense of “I’m not sure why, but something about this don’t feel right.” When that happens, you owe to yourself to pause and pay attention to the tension. Pause and ask yourself, “What about this bothers me?” Decide to pause even when you can’t pin-point the cause of your hesitation. Explore, rather than ignore your conscience.
• The Maturity Question. What is the wise thing to do? An option can be both not wrong and unwise at the same time. An option can be both not illegal and unwise at the same time. An option can be both not immoral and unwise at the same time. Ask yourself, in the light of my past experiences, my current circumstances, and my future hopes and dreams, what is the wise thing for me to do?
• The Relationship Question. What does love require of me? If you are to take advice from someone a lot wiser than me, consider these words: ‘Love is patient and kind. Love is not jealous or boastful or proud or rude. It does not demand its own way. It is not irritable, and it keeps no record of being wronged.’ ( 1 Corinthians 13:4-5). Love requires Patience. Love is not pushy, Love requires that I move at others’s pace rather than requiring others to move at mine. Love requires kindness. Kindness is love’s response to weakness. Kindness is the choice to loan others our strength rather than reminding them of their weaknesses. It’s doing for other what they cannot in that moment do for themselves. Love requires to keep envy and pride from interfering with our ability to celebrate the success of others. Love requires us to allow other to shine. Decide with the interests of others in mind.

Asking Questions, Psychological Safety, Focus and Energy

Psychological safety is the belief that the team is safe for interpersonal risk taking. That one will not be punished or humiliated for speaking up with ideas, questions, concerns, or mistakes (Edmondson, A. C., The fearless organization, 2018).

Conflict arises in every team, but psychological safety makes it possible to channel that energy into productive interaction, that is, constructive disagreement, and an open exchange of ideas, and leaning from different points of view.

Edmondson, A. C., The fearless organization (2018).

Creating psychological safety is not abound being nice to each other or reducing performance standards, but rather about creating a culture of openness where teammates can share learning, be direct, take risks, admit they “screwed up,” and are willing to ask for help when they’re in over their head (Mastrogiacomo, S., Osterwalder, A., Smith, A., & Papadakos, T., High-impact tools for teams, 2021).

Crafting the right questions is central to gaining more in-depth insight, inspiring forward movement, and bringing focus and energy (Smutny, M., Thrive: The Facilitator’s Guide to Radically Inclusive Meetings, 2019). You can develop your own questions based on your knowledge of the team dynamics, or you can experiment with methods like Appreciative Inquiry (Cooperrider, D. L., Whitney, D., & Stavros, J. M., 2008), World Café (Brown, J., & Isaacs, D., 2005), or Open Space Technology (Owen, H., 2008).

Here are few principles adapted from World Café:

1. Set the Context. Attend to why you are brining people together and what you want to achieve. Context includes who should attend, what questions will generate the most creativity, and how the design of the harvest.
2. Create Hospitable Space. Meeting spaces make a difference. You want one that feels safe and inviting. When people feel comfortable, they think creatively and listen better.
3. Explore questions that matter. Craft questions relevant to the real-life concerns of the group. Powerful questions attract collective energy, insight, wisdom, and action. The most powerful questions are open-ended, invite curiosity, and emerge from the lives of the people involved.
4. Encourage Everyone’s Contribution. Welcoming every participants contribution is central to a World Café. Recognise that every has ideas and thoughts to share. Nonetheless, some people prefer only to listen. The World Café method provides a structure for both sharing and listening.
5. Connect Diverse Perspectives. New ideas and discoveries develop as participants move between tables and meet new people. New Perspectives, insights, and recognition emerge.
6. Listen Together for Patterns and Insights. Listening well determine the success of a World Café. By listening and paying attention to themes, patterns, and insights, the whole group discovers wisdom. People see new connections, shared themes, and insights.
7. Share Collective Discoveries. Conversation at one table connect with conversations at other tables. The harvest makes these connections visible to the whole group. Encourage a few minutes of silent reflection on the patterns, themes, and deeper questions experienced in the three rounds of small group conversation. Then, invite the larger group to share common insights and discoveries. Capture the harvest by working with notes and a graphic recorder.

Asking Questions and the Art of Listening

Anytime moving parts are out of alignment, it causes friction, which can shake your organization apart. Friction causes wear and tear on the people who work there and the people you serve. Everyone genuinely wants to prove his worth, impress people with great ideas, or just plain old fix things. Most of the time professionals are so busy trying to contribute their ideas and get other people to change that they don’t realize they’ve spent zero time understanding those other people and listening to them. No one is listening because everyone thinks others need to understand what he has to say. Consequently, understanding what is going on in other people’s minds is the first step toward counterbalancing the fascination of numbers and familiar perspectives. (Young, I., Practical Empathy, 2019).

There is no point in asking questions if you’re not ready, willing, or able to listen. So we need to become better listeners before getting better at asking questions.

Listening and Better Understanding

Really listening lets you understand someone — or a situation — on several different levels. This leads to better understanding and gives you deeper and more detailed information to use in your work (Brooks, K., & Quesenbery, W., Storytelling for User Experience. 2014):

• Really listening lets you hear subtext and overtones. You can hear not just what people are saying, but also the way they say it. This second layer can give you a deeper sense of who they are, what’s important to them, and how they view the world.
• Really listening allows people to share their deeper thoughts. When you listen and observe carefully, you can hear and see the way people shape their thoughts, how they think about what they are about to say, and how they respond to hearing themselves say it. In this way, listening empowers speakers to spake with more awareness of what they are saying and to take the time to consider what they mean carefully.
• Really listening lets people know that are being heard. The listener empowers the speaker to share thoughts and observations they might otherwise keep to themselves. This can be especially important in situations where people have not been heard in the past — for example, in the relationship between a company and its customers.

Listening and Trust

In a previous post, we discussed the importance of building trust to influence our stakeholders.

Trust must be earned and deserved. You must do something to give the other people the evidence on which they can base their decision on whether to trust you. You must be willing to give in order to get.

There are two important things about building trust. First, it has to do with keeping one’s self interest in check, and, second trust can be won or lost very rapidly (Maister, D. H., Galford, R., & Green, C, 2021).

Effective trusted advisors are (it should be no surprise to designers) very good listeners. Listening is not a sufficient condition by itself, but it is a necessary one, the second step in the Trusted Advisor’s five state process:

1. Engage: Let’s talk about…
2. Listen: Tell me more…
3. Frame: So the issue is…
4. Envision: Let’s imagine…
5. Commit: I suggest we…

Listening is essential to “earn the right” to comment on and be involved in the client’s issues. We must listen effectively, and be perceived to be listening effectively, before we can proceed with any advisory process. Cutting the chase without having earned the right to do so will usually be interpreted as arrogance.

Maister, D. H., Galford, R., & Green, C. “The Art of Listening” in The trusted advisor, (2021)

A trusted advisor might say, “What I like about your idea is X; now help me understand how can we use it to accomplish Y.” Through such language, the advisor constantly lets the client know that the client is respected and that the two of them are free to discuss with great candor the specific merits of the idea at hand (Maister, D. H., Galford, R., & Green, C, The trusted advisor, 2021).

The Right Questions at the Right Time

That said, it’s essential to understand what kinds of conversations the team needs to have at different phases of the product development lifecycle. Understanding what the team is trying to achieve at each phase of the lifecycle will help you figure out the questions that trigger the right conversations at the right time. The reason is that — unless you’ve built a lot of trust and reputation with your stakeholders — questions out of place might be perceived as annoying.

That said, I encourage you to — after listening and spending time to understand what the team is trying to achieve — ask the hard questions that clarify if the team is working toward their vision and their goals or not.

My colleagues Edmund Azigi and Patrick Ashamalla have created a great set of questions and a cheat sheet that maps which questions are more appropriate for different phases of the product development lifecycle. I’ll list if few here:

• Discover: What are the personas? What key problems do we need to solve?? What does success look like?? What project constraints have been identified?? What are competitors doing? 
• Define: Do the concepts designs achieve business and user goals? Has there been a technical feasibility review?
• Develop: Has there been a technical feasibility review? Has a usability test been scheduled? What are the tasks accomplished during usability testing? Will the detailed designs achieve business and user goals? Have custom controls defined, approved, scheduled to build in our design system? Do final designs meet consistency standards?
• Deliver: Have any technical feasibility issues arisen? Is testing complete? Have the UX bugs/defects been documented, prioritized, and resolved? Has performance been assessed? Do the coded pages match the design?

Getting Better at Asking Questions

The hardest part of getting better at asking questions is to do this habitually. It’s easy to become better at asking questions during a structured questioning exercise, but to have an impact, the behavior has to become routine. It should be part of the way we do our jobs. It should be part of how we do our jobs and incorporated into our everyday interactions with others. And for that to happen, we must come to terms with five forces that get in the way of questioning (Berger, W., The book of beautiful questions, 2019):

• Am I willing to be seen as naïve?
• Am I comfortable raising questions with no immediate answers?
• Am I willing to move away from what I know?
• Am I open to admitting I might be wrong?
• Am I willing to slow down and consider?

Design Strategist Multiplication Program

As I mentioned in the first post of this series, my colleague Edmund Azigi and I are designing a Design Strategist Multiplier program per the request of Scott Lietzke, our VP of Design at SAP SuccessFactors, to help designers pick up the skills to influence product strategy and decisions that help drive product vision forward.

Such a program is practice-based, accompanied by a series of seminars, corresponding required reading, and reflective practice journaling to create opportunities for people to grow.

In the following posts, I will discuss facilitation and making good decisions.

Recommended Reading

Annamalai, Nagappan; Kamaruddin, Shahrul; Azid, Ishak Abdul; Yeoh, TS (September 2013). “Importance of Problem Statement in Solving Industry Problems”. Applied Mechanics and Materials. Zurich. 421: 857–863. doi:10.4028/www.scientific.net/AMM.421.857. S2CID 60791623

Berger, W. (2019). The book of beautiful questions: The powerful questions that will help you decide, create, connect, and lead. New York, NY: Bloomsbury Publishing.

Berkun, S. (2008). Making things happen: Mastering project management. Sebastopol, CA: O’Reilly Media.

Bland, D. J., & Osterwalder, A. (2020). Testing business ideas: A field guide for rapid experimentation. Standards Information Network.

Brooks, K., & Quesenbery, W. (2014). Storytelling for User Experience: Crafting Stories for Better Design. New York, USA: Rosenfeld Media.

Brown, J., & Isaacs, D. (2005). The world cafe: Shaping our futures through conversations that matter. San Francisco, CA: Berrett-Koehler.

Cooperrider, D. L., Whitney, D., & Stavros, J. M. (2008). The appreciative inquiry handbook: For leaders of change. Berrett-Koehler.

Calabretta, G., Erp, J. V., Hille, M., (2016). “Designing Transitions: Pivoting Complex Innovation” in Strategic Design: 8 Essential Practices Every Strategic Designer Must Master. Calabretta, G., Gemser, G., & Karpen, I. Amsterdam, Netherlands: BIS Publishers B.V. 

De Bono, E. (2015). Lateral Thinking: Creativity Step by Step (Reissue edition). London, England: Harper Colophon.

DeGrandis, D. (2017). Making work visible: Exposing time theft to optimize workflow. Portland, OR: IT Revolution Press.

Desjardins, J., (2021), Every Single Cognitive Bias in One Infographic, retrieved September 13, 2021 from Visual Capitalist website: https://www.visualcapitalist.com/every-single-cognitive-bias/

Edmondson, A. C. (2018). The fearless organization: Creating psychological safety in the workplace for learning, innovation, and growth. Nashville, TN: John Wiley & Sons.

Garrett, J., (2010), “The Elements of User Experience: User-Centered Design for the Web and Beyond“, 192 pages, New Riders; 2nd edition (16 Dec. 2010)

Gothelf, J. (2019, November 8). The hypothesis prioritization canvas. Retrieved April 25, 2021, from Jeffgothelf.com website: https://jeffgothelf.com/blog/the-hypothesis-prioritization-canvas/

Gothelf, J., & Seiden, J. (2013). Lean UX: Applying lean principles to improve user experience. Sebastopol, CA: O’Reilly Media

Govella, A. (2019). Collaborative Product Design: Help any team build a better experience. Sebastopol, CA: O’Reilly Media.

Govindarajan, V., & Trimble, C. (2010). The other side of innovation: Solving the execution challenge. Boston, MA: Harvard Business Review Press.

Hammond, John S., Ralph L. Keeney, and Howard Raiffa (2013). The Hidden Traps in Decision Making in HBR’s 10 Must Reads on Making Smart Decisions, 192 pages, Harvard Business Review Press (March 12, 2013)

Harvard Business Review, Kahneman, D., & Charan, R. (2013). HBR’s 10 must reads on making smart decisions. Boston, MA: Harvard Business Review Press.

Hoffman, K. M. (2018). Meeting Design: For Managers, Makers, and Everyone. Two Waves Books.

IBM Enterprise Design Thinking. (2018). Assumptions and Questions. Retrieved February 15, 2022, from Ibm.com website: https://www.ibm.com/design/thinking/page/toolkit/activity/assumptions-and-questions

Kalbach, J. (2020), “Mapping Experiences: A Guide to Creating Value through Journeys, Blueprints, and Diagrams“, 440 pages, O’Reilly Media; 2nd edition (15 December 2020)

Lafley, A.G., Martin, R. L., (2013), “Playing to Win: How Strategy Really Works”, 272 pages, Publisher: Harvard Business Review Press (5 Feb 2013)

Mastrogiacomo, S., Osterwalder, A., Smith, A., & Papadakos, T. (2021). High-impact tools for teams: 5 Tools to align team members, build trust, and get results fast. Nashville, TN: John Wiley & Sons.

Medeiros, I. (2021, May 9). Strategy and the Importance of Vision. Retrieved April 26, 2021, from {design@ative} website: https://www.designative.info/2021/05/09/strategy-importance-of-vision/

Medeiros, I. (2021, March 27). Strategy and Stakeholder Management. Retrieved April 26, 2021, from {design@tive} website: https://www.designative.info/2021/03/27/strategy-and-stakeholder-management/

Mueller, S., & Dhar, J. (2019). The decision maker’s playbook: 12 Mental tactics for thinking more clearly, navigating uncertainty, and making smarter choices. Harlow, England: FT Publishing International.

Natoli, J. (2015). Think first: My no-nonsense approach to creating successful products, memorable user experiences + very happy customers. Bookbaby.

Owen, H. (2008). Open Space Technology: A User’s Guide (3rd ed.). San Francisco, CA: Berrett-Koehler.

Perri, M. (2019). Escaping the build trap. Sebastopol, CA: O’Reilly Media.

Pohlmann, T., & Thomas, N. M. (2015, March 27). Relearning the art of asking questions. Harvard Business Review. Retrieved from https://hbr.org/2015/03/relearning-the-art-of-asking-questions

Rettig, M., (2010) “Design a Vase”, in “An evening of conversation about Design, Interaction, Work and Life“, May 25th, 2010, IxDA Gathering, 399, Pu DianRoad, Pudong New District, Shanghai, 200122, P.R. China

Shapiro, S. (2020). Invisible solutions: 25 Lenses that reframe and help solve difficult business problems. Herndon, VA: Amplify Publishing (March 3, 2020).

Sloane, P. (2017). The leader’s guide to lateral thinking skills: Unlock the creativity and innovation in you and your team (3rd ed.). London, England: Kogan Page.

Smutny, M. (2019). Thrive: The Facilitator’s Guide to Radically Inclusive Meetings. Bothell, WA: Civic Reinventions, Inc. (August 10, 2019).

Stanley, A. (2020). Better decisions, fewer regrets: 5 Questions to help you determine your next move. Grand Rapids, MI: Zondervan.

Wedell-Wedellsborg, T., (2020) “The Elevator Problem”, in What’sYour Problem?: To Solve Your Toughest Problems, Change the Problems You Solve, 215 pages, Publisher: Ingram Publisher Services (17 Mar 2020)

Young, I. (2019). Practical Empathy. Brooklyn, New York: Rosenfeld Media.