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8 creative solutions to your most challenging problems

July 30, 2021 - 25 min read


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What is problem-solving?

An 8 step approach to inside-out problem solving

Other problem-solving tips

It’s time to tackle your 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 encounter them on a personal level.

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

Fortunately, problem-solving is a skill people can develop over time.

In this article, we’ll explore the art and science of problem-solving, skills a good problem-solver should have, and eight steps to solve problems better.


What is problem-solving?

Problem-solving involves defining some issue you need to address. From there, you find out what caused it and why. Then, you can generate a solution.

Being a strong problem-solver helps you identify the root cause of issues so you can fix them instead of applying band-aid solutions.

Good problem-solving also helps strengthen business and personal relationships. You’re able to come up with solutions that address the problem while benefiting everyone.

Also, the problem-solving process increases a solution's chances of working by reducing unknowns.

According to author and authority on visual thinking, Tom Wujec, “We intuitively know how to break down complex things into simple things and then bring them back together again.” By doing so, you can reduce the unknowns associated with a problem’s complexity.

Tom outlines an eight-step approach in his popular TED talk that makes solving problems as straightforward as making toast (almost). All you need are 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, you’re bound to elevate your solution’s quality. 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.

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

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

However, let’s first go over a few skills one should have to be a strong problem-solver.

Problem-solving skills

Problem-solving itself is a skill. However, those involved in solving problems would be wise to learn other skills complementary to problem-solving.

Here are some key skills to have.


Small problems you experience frequently can often be solved with relative ease. You’ll have a standard method of approaching the issue.

However, you might not have procedures in place for larger or more novel problems. In this case, creativity comes into play.

Out-of-the-box thinking can generate excellent solutions outside of those available to you. It pushes you to develop bolder approaches to thinking and doing. Creative thinking enables you to challenge current ideas and understand the urgency, relevance, and purpose of new solutions.


Part of problem-solving is generating multiple ideas for solutions. Then, you weigh their pros and cons.

At some point, however, you must choose a solution and move forward with it. Yet, with several alternatives and solutions to problems, one could struggle to choose.

Consequently, those involved in problem-solving must be decisive. They can’t be timid in picking a solution and trying it, or no one will ever solve the problem.

Even if a solution fails, you can confidently cross it off your list and move on knowing you were brave enough to try it.


Research abilities are essential to problem-solving. You must be able to dig deep into the problem and find out what’s causing it.

This could involve looking into things yourself and seeking answers from others. On the latter point, knowing how to ask the right questions will be invaluable.

Research skills are also necessary for finding solutions. You should be able to seek out more knowledgeable colleagues about possible solutions, but online research skills are a must as well. It’s important to search for a variety of recently published sources that reinforce and build upon each other, ranging from reflective articles written by leaders themselves to research and case studies highlighting companies more objectively.

Emotional intelligence

As we’ll get into later, you’ll need to work with several stakeholders (such as team members, consumers, and shareholders) to arrive at solutions to problems that benefit everyone.

Emotional intelligence is a vital skill to have. High emotional intelligence helps you cooperate with others on finding and implementing solutions. It also aids in considering perspectives outside your own in case you’re biased toward your own idea.

For the same reason, emotional intelligence helps with compromise.


Persuasion is a more important skill than you might think in problem-solving. It is an influencing tactic that enables others to frame and approach challenges from your perspective. At its core, persuasion encourages people to align their vision for problem-solving with yours.

Once you come up with a couple of solutions to problems, you must persuade your fellow teammates that they’ll work. Additionally, you must persuade your boss, clients, or other stakeholders that your solution will fix the problem.

Effective methods of persuasion include forming a coalition with other team members who advocate your solution and collecting evidence in support of it. Evidence will help rationalize and legitimize your solution by grounding it in concrete examples that showcase its successful track record in the past.

When finding solutions to problems, persuasion is a better technique than power for building agreement with other teammates. Attempting to use power to force people to accept a solution — especially when they believe they have a better solution — will backfire.

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 I can’t emphasize it 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 correct problems can be harder than solving them once defined. In psychology, countless studies show that how we frame a problem influences our decision-making and behavior. Psychologists call this the framing effect for obvious reasons.

In practice: Make time for intentional inquiry upfront. Ask your team, “Are we solving the right problem?”

Leave space for dialogue. Try to talk 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, defining a problem is like, as Amy says, peeling back an onion’s layers and getting closer to the root cause each time.


2. Check your mindset

In addition to viewing the problem as an opportunity, try approaching it with curiosity.

This means viewing it objectively, without judgment. You must be in a state of mind where you’re prepared to be surprised and delighted by novel solutions that 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 an observer’s perspective, the goal is not to judge the situation (“Oh, this is a disaster!”), or solve it immediately (“I know what to do, and there is no time to waste!”). Rather, your aim is to 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. You’ll be an objective observer who's interested in learning more about the problem and how to solve it.

Of course, if you’re facing an urgent situation, this doesn’t mean you should lollygag. You can achieve this practice in a matter of minutes. Mindful moments, even in a setting of urgency like the Emergency Room, can significantly benefit your well-being and mental fitness.


3. Empathize with the players

On a product team, the designer will interview all stakeholders early in the design cycle to empathize with each of their experiences. On an individual level, the stakeholder could mean your team, the buyer, and almost always, yourself.

That last one, empathizing with yourself, is a step many often overlook.

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 effectively, 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. 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 encourage and motivate.

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.

Logically, we’d work harder to move through a challenge when we can meaningfully answer the questions, “What’s the point?” and “Why does it matter?”

more-innovative-solutions-to- problems

According to Deloitte’s Insights 2020 Global Marketing Trends Report, purpose-oriented companies report an average of 30% more innovation, not to mention 40% more workforce retention.

Knowing your purpose and connecting it to the problem at hand helps tie things together. It gives you a “why” for solving the problem in the first place, which can lead to more innovative solutions to problems like Deloitte found.

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 individuals frequently overlook it. 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.

Now, consider having your team members brainstorm individually, at least before you come together for group brainstorming.

Studies from the early 2000s have shown people generate more (and better) ideas when brainstorming alone. This is likely due to the absence of judgment for out-of-the-box ideas, comfort exploring unconventional ideas, and a lack of being put on the spot.

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.

However, what is a small bet?

Eric Barker, the author of the best-selling book Barking Up the Wrong Tree, 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 one or two possible solutions from your brainstorm in step five to test in a way that stretches but doesn’t overwhelm you, your team, or your resources. Choose progress over perfection. You can always improve your solutions later if necessary.


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.

An MVP is a product with the bare minimum features to attract early adopters and gain feedback, but not so many features that it’s too expensive to create or redo after feedback.

In executive coaching, it’s common for a coach to encourage a leader to take on one new micro-action for a defined period to test efficacy, impact, and viability.

7. Get feedback/evaluate options

It’s essential 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 to measure a solution’s effectiveness.

On an individual level, determine one measure through which you can assess whether or not your bet is effective. One example, which 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 the average number of steps calculated by week on your Fitbit or wellness app to assess your success and trajectory.

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

It’s all about consistent learning and growth for high-functioning design teams, leaders, and peak performers. 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.”


Other problem-solving tips

Prepare for the worst possible outcomes

Prepare for the worst possible outcome of each idea.

Of course, you aren’t hoping that your ideas crash and burn — and it’s fine to come up with out-of-the-box ideas that are risky — but you want to be prepared for the eventuality that your ideas don’t work.

Why? By doing "pre-mortem" planning, you can be better prepared to adjust your approach, to contain and mitigate risk, and to get more valuable learning out of the experiment.

As you generate ideas, think to yourself, “how could this decision possibly go wrong, and how bad would it be if it did?”

Consider it from multiple perspectives and write down all the possible ways things could go awry.

However, keep in mind that just because an idea has a drastic potential downside doesn’t mean it’s a bad idea. The downside might have a slim chance of happening — just be ready for it.

Document everything

It’s vital to document everything in your problem-solving process. That way, you’ll have written notes on various ideas to try in case one doesn’t solve the problem.

By documenting everything, you can also keep detailed notes about each solution. This will help you think through the details.

When brainstorming with colleagues, make sure everyone is writing every idea they come up with down on paper. Do this in conjunction with the whiteboard if possible.

At the same time, people can write down any thoughts that come to mind as others are talking or sharing their ideas.

For every idea, have everyone write down the details of each solution and their potential implications, too.

Give yourself a tighter deadline

Parkinson’s Law says that work expands to fill the time allotted. In other words, if we give ourselves a week to do something, like solve a problem, it’ll take a week to accomplish that goal.

This phenomenon isn’t exactly scientific, but you may notice it throughout your life whenever you have a deadline.

Our tendency to procrastinate can cause it. Alternatively, we may fail to estimate how long something would take. That forces us to cram in a bunch of work last-minute.

Either way, use Parkinson’s Law to your advantage by giving yourself a shorter deadline to solve the problem. Doing so can force you to find a workable solution faster.

It’s time to tackle your problems

Solving problems effectively takes several skills and a relatively regimented process. Make sure you know your problem, consider your stakeholders, and connect the problem to your purpose before generating ideas.

Once you come up with a few ideas, implement them right away, and get feedback fast.

Following the above process should help you develop solutions to any problem you come across with confidence and optimism.

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Published July 30, 2021

Sarah Greenberg, M.Ed, MA, MFT, BCC

Director of Clinical Design & Partnerships, BetterUp

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