Sarah Greenberg

Lead Coach at BetterUp

Posted in: Wisdom & Mindfulness


8 Creative Solutions to Your Most Challenging Problems

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8 Creative Solutions to Your Most Challenging Problems

I work with some of the most talented rising leaders in Silicon Valley. Like all of us, they face problems. Sometimes, they face them as leaders within their organizations, and sometimes they face them on a personal level.

While the last decade has introduced many helpful frameworks for solving complex organizational challenges, creatively, what my coachees really want and need are the skills to help them address challenges holistically, at work and in life.

Fortunately, problem solving is a skill that can be developed. According to Tom Wujec, “We intuitively know how to break down complex things into simple things and then bring them back together again.” In his popular TED talk, Tom outlines an 8 step approach that makes solving problems as straightforward as making toast (almost). All you need is some drawing materials, collaborative colleagues, and a willingness to get granular.

The way Tom employs design thinking for solving complex business challenges is brilliant. Yet, one ingredient that’s missing from his approach is inner work. When you engage in the kind of internal work that ignites clarity, creativity, and resilience, the quality of your solution is bound to be elevated. That’s one reason I (and BetterUp) passionately endorse doing inner work, even at work. What we need are frameworks that apply to both business problems and personal challenges.

What we need are frameworks that apply to both business problems and personal challenges. Click To Tweet

To bridge the gap between existing models and a new approach that focuses on priming the mindset of the problem solver before getting to the solutions, I sat down with our senior designer and product manager, Amy Aaron. Our goal was to come up with a simple framework to problem solving that synthesizes the best of applied design thinking with evidence-based coaching.

What we discovered early in our conversation is a significant overlap between how high powered design teams approach problems and the strategies that psychologists and leadership coaches recommend for tackling challenges. These 8 steps will help you find creative solutions to your most challenging problems both personally and professionally.

An 8 Step Approach to Inside Out Problem Solving

1. Define the (right) problem

How we frame a problem significantly influences our decision making and behavior.

This first step is a classic, and can’t be emphasized enough.

In design, you never kick off a project without articulating the problem. It’s the first step in any design cycle. Individuals often come to coaches with a specific “problem” in mind. Through a coach, you can get a deeper understanding of the root cause versus the symptom. In business, diagnosing the right problems can be harder than solving them once defined. In psychology, countless studies show that how we frame a problem significantly influences our decision making and behavior.

In practice: Make time for intentional inquiry upfront. Ask your team, “Are we solving the right problem?” Leave space for dialogue. Try to dialogue with a trusted friend or coach, reflecting on the questions, “Is the problem really what I think is? What else could it be?” Whether on a team or as an individual, the process of defining a problem is like, as Amy says, peeling back the layers of the onion, and getting closer to the root cause each time.

Defining a problem is like peeling back the layers of the onion, and getting closer to the root cause each time.Click To Tweet

2. Check your mindset

In addition to viewing the problem as an opportunity, try approaching it with curiosity. This means viewing it objectively, without judgement, in a state of mind that is prepared to be surprised and delighted by what novel solutions lie on the other side of this problem.

In practice: Try tuning up what in a mindfulness practice might be referred to as the “observing mind.” When viewing a problem from the perspective of an observer, the goal is not to judge the problem (“Oh this is a disaster!”), or solve it immediately (“I know what to do and there is no time to waste!”), but rather be with it as it is, not as you want it to be (“Huh, this is interesting. Let me explore the details and understand further.”). By putting yourself in an observing, curious state, you’ll likely find more space for a novel perspective. Of course, if you’re facing an urgent situation, this doesn’t mean you should lolligag. This practice can be achieved in a matter of minutes or moments. Mindful moments, even in a setting of urgency like the Emergency Room, can have great benefit on your well-being and on outcomes.

3. Empathize with the players

Empathizing with the stakeholder could mean with your team, with the buyer, and almost always, with yourself. Click To Tweet

On a product team, the designer will interview all of the stakeholders early in the design cycle in order to empathize with each of their experiences. On an individual level, empathizing with the stakeholder could mean with your team, with the buyer, and almost always, with yourself. This last one, empathizing with yourself, is a step that’s often overlooked. Renowned researcher Kristin Neff defines self-empathy as self-compassion. Instead of being hard on ourselves for having a problem, or not dealing with it quickly/effectively/brilliantly enough, self-compassion means treating ourselves as we might a best friend, in a manner that is encouraging and motivating.

In practice: Make a “thought experiment” to consider your problem from other perspectives. Start by writing a list of all those who are impacted by this challenge. Next, take one minute per stakeholder to visualize yourself in their shoes. When you get to yourself, it’s no longer a leap to imagine yourself in your shoes. But it might be a leap to view yourself with compassion. Try to get a sense of how you’re speaking to yourself about this challenge, and if you notice you’re being less than encouraging, shift what psychologists call your “self-talk,” to be more aligned with how you might talk to a best friend when you aim to be encouraging and motivating. Note that this practice is simple, but not easy. Do your best, and note your insights.

4. Connect with your purpose

According to psychologist and researcher Angela Duckworth, grit + purpose = success. It’s logical that we’d work harder to move through a challenge when we can meaningfully answer the question, “What’s the point?”

In practice: For actionable tips on how to hone purpose check out our post and tip sheet on how to make stress work for you.

5. Generate ideas

Complex problems demand agile game plans and strategies. If there was one straightforward solution, you probably wouldn’t consider the problem complex. Spending time generating ideas is a common activity in organizations (especially on creative teams), but it’s frequently overlooked by individuals. Often, a coach will spend part of a session supporting an individual to connect with their inner wisdom and generate a multitude of options they may not have considered.

In practice: It’s time to whiteboard! Gather around a whiteboard or grab a giant sheet of craft paper, and start jotting down potential solutions to the problem you defined. Consider questions such as “What would I do if there were no monetary or time constraints?” or “What is the wackiest idea?” to get the juices flowing. Revisit the empathy step above, and consider solutions that would solve the problem from each perspective.

6. Make small bets

Generating ideas isn’t simply an intellectual exercise. It sets you up to take action. Rather than ruminating, experiment, and test the success of an idea by putting it into action. What is a small bet? Author of the best selling book, Barking Up the Wrong Tree, Eric Barker, defines it as “A small experiment that tests a theory. It’s just big enough to give you the answer you need but not so big that it wastes too much precious time, money, or resources.”

In practice: Choose 1-2 possible solutions from your brainstorm in step 5 to test, in a way that stretches but doesn’t overwhelm you, your team, or your resources. Choose progress over perfection. In the product world, we refer to this as MVP mode, or “minimum viable product,” a term popularized by the Lean Start-Up methodology proposed by Eric Ries in 2013. In executive coaching, it’s common for a coach to encourage a leader to take on one new micro-action for a defined period of time in order to test efficacy, impact, and viability.

7. Get feedback/evaluate outcomes

It’s important to have a way to qualitatively or quantitatively assess the impact of your small bets. As a leader in your organization, make sure you have a defined KPI. On an individual level, determine one measure through which you can assess whether or not your bet is effective. One example that requires no complex assessment is setting up a “self-report measure” that will show changes based on an established baseline. For instance, if you’re working to increase your activity level, you may use average number of steps calculated by week on your Fitbit to assess success. In evidence-based coaching, we use scientifically-developed assessments to track progress so we can regularly tweak an approach, but also quickly recognize when an approach is working.

In practice: Determine your measure of success or KPI. If you’re torn between multiple choices, err on the side of simplicity. If you’re working with a coach, you can ask for their recommendations for how to track and assess progress.

8. Start again

For high functioning design teams, leaders, and peak performers, it’s all about consistent learning, and growth. In this model, failure is good, as long as you learn from it.

As John Foster Dulles, Former US Secretary of State put it, “The measure of success is not whether you have a tough problem to deal with, but whether it is the same problem you had last year.”


Special thanks to BetterUp senior designer and product manager, Amy Aaron.

Original art by Theo Payne.

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