The Art of Problem-Solving: 4 Creative Strategies to Tackle Your Biggest Obstacles

Problems never stop.

To be alive means constant challenges, big and small. Life’s question for you is not, how can I avoid problems, but, how can I eat problems for breakfast? I’m sure you’re dealing with multiple problems today, from what to wear to how to find more clients, to last night’s fight with your partner.

It’s tempting to throw up your hands, but when you cultivate a growth mindset you can learn to love your problems. If knowledge is power, then these 4 creative problem-solving strategies will help you unlock your hidden strength.

3 Types of Problems

Problems come in three flavors:

1. Setbacks and failures: Why did my car break down? Why is company revenue down 20 percent? Why am I so tired all the time?
2. Goals: How can I attract 10 more clients this month? What’s the best way to clean out my garage? How can I convince him to date me?
3. Decisions: Should I move to Finland? Should I confront my boss? Leave the toxic relationship? Go to Dave’s pool party or Mel’s dinner? 

Rather than dump a bunch of problem-solving strategies in your lap, let’s look at four real-ish case studies and use them to illustrate our four new strategies. 

1. Six Thinking Hats

The scenario: You are an e-commerce solopreneur, and your startup teaches aspiring speakers how to book paid gigs with corporate clients. You launched this side hustle in 2017 but recently left your salaried job to take this business seriously. 

The problem: Revenue was $50,000 last year, but 2021 is off to a slow start; you sold zero training packages in January and February. You made the tough decision to let go of your one part-time employee. Your goal is to turn the ship around and double revenue to $100,000 by the end of the year.

The problem-solving strategy: Six Thinking Hats

Here you have a problem (flagging revenue) and a goal (sales target). Doubling revenue is ambitious even in a healthy economy, so a bold strategy and massive action is needed. 

You might be tempted to take immediate action and work twice as hard, but your efforts are more likely to succeed if you slow down. Thankfully, there are excellent frameworks for thinking methodically, and Six Thinking Hats is among the most reliable.

How it works: 

In 1985 Edward De Bono published Six Thinking Hats. In it, he observed that our brains can think in several different modes depending on our aims. In this moment, we might use deduction to figure out why the lawnmower won’t start. Later, we might design a more reliable engine. That night, you imagine hiring a gardener.

De Bono organized thinking styles into six categories, represented by colored hats:

Blue hat: One hat to rule them all! This exercise can be done in groups or alone. It starts with the imaginary blue hat, which calls for high-level leadership thinking. We clarify: what’s the problem (revenue is down); what’s our goal (earn $100,000); and what is our first priority?

White hat: Just the facts, ma’am. Here we stick to logical, fact-based thinking. We review key performance indicators and note: 

• First-quarter 2021 revenue was only $3,000, down 71%.
• Paradoxically, website visits increased 38% because of massive new search engine traffic to two blog posts.
• The lion’s share of our sales comes from email marketing, but very few blog readers (1%) subscribe.
• Many new visitors are arriving from the U.K. and Australia.

Green hat: There are no dumb ideas. Green is the creative hat. In this phase, we brainstorm new or “crazy” ideas, seek elegant solutions, alternatives and opportunities. As a solopreneur, you do this alone, and here’s what comes up:

• What if we create a new offer for website visitors arriving at our two most popular blog posts to capture more subscribers?
• What if we create a new offer for visitors from the U.K. and Australia?
• What if we host more free workshops to build trust?
• What if we created pre-recorded courses instead of live webinars?

Yellow hat: The future is bright. This is the optimist hat; while wearing it, you imagine all potential benefits tied to Green Hat ideas.

• If we increase our email subscriber rate from 1% to just 2%, we could capture 150 additional leads each month just from our top two blog posts.
• If we create a special offer for British and Australian visitors, we could sign five new clients per month.
• Our last free webinar recruited 95 new hot leads. Repeat this and we could create five to 10 new clients per month.
• Adding pre-recorded content to our service lineup means passive, recurring revenue, with fewer expenses. This could mean $3,000 in new revenue monthly or one-third of our $100,000 goal.

Red hat: Go with your gut. Under this hat, you’re free to explore feelings and hunches, fears and excitement. 

• You sense that your ideal clients are those who experienced your training live before making a purchase.
• Your gut says email marketing has huge potential if only you’d double your efforts here.
• You feel that chasing customers from overseas will be fruitless.
• You believe that creating on-demand virtual training courses will be popular, but you fear that hiring a video editor and web designer will eat up profits.

Black hat: Danger, Will Robinson. This is the cap of caution, the sombrero of sober thought. Careful entrepreneurs ask, “What could go wrong?” then act to manage risks. We note:

• Hosting free workshops requires time and money with no guarantee of sales.
• Getting better at email marketing means switching to paid plans for both Mailchimp and pop-up software. Can we cut costs elsewhere?
• You’re not sure about how your trainers will feel about turning their recorded sessions into on-demand products—or whether you can do that without getting sued. Let’s talk to our lawyer.

This process should be done on paper, and you only need to spend two to five minutes under each hat. The Six Thinking Hats method forces disciplined thinking and delivers better decisions, faster. 

When using it in a group, it will help you sidestep adversarial thinking, where each person entrenches on a side. This process won’t feel natural at first, so practice.

Strategy 2: The McKinsey Method, Featuring the Issue Tree

The scenario: You recently left a teaching job to become a financial coach, and you’re wondering how to find clients.

The problem: You had a crop of clients when you launched early last year, but the pipeline dried up, and you’re struggling with monthly bills. Half your clients continue to return, but the other half disappear without warning.

The problem-solving strategy: The McKinsey Method and Issue Tree

In this scenario, you again have a problem—lack of clients—and an opportunity to set a goal. You look at your monthly budget and see that by signing only two new clients per month, you can not only cover your expenses, but also stash some cash. 

This is a complicated challenge because there are many potential causes and solutions. We need to approach it with a framework that is efficient and thorough.

How it works:

Global consulting firm McKinsey & Co. has worked with top companies worldwide since 1926 to solve their most intractable problems. Naturally, its people have to be exceptional problem solvers. Lucky for us, many of them have pulled back the curtain to share their methods. 

Step 1: Generate a hypothesis. The McKinsey method starts by formulating a hypothesis about the problem using our intuition. In this scenario, we guess that we’re not seeing the number of clients we want because we’re not generating nearly enough leads. And we’re not attracting the type of clients we want because we’re talking to the wrong leads. Now we have some ideas we can test with hard data.

Step 2: Create a map of the problem. Solving a problem like this requires a complete picture of all of its facets. The Issue Tree (or Logic Tree) is the perfect tool for mapping out the challenge at hand. It will guide your research and prevent you from stumbling down dead-end alleys. It will help you identify the most likely cause and solutions, and move to action quickly. 

You can use any free mind mapping tool to create issue trees. I like Mindmeister. An issue tree looks like this:

A good issue tree is MECE: mutually exclusive and collectively exhaustive. Don’t sweat the jargon—all this means is that the issue tree should capture all facets of the problem and that none of the boxes overlap.

In our scenario, we might start like this:

The blue box captures the problem concisely, and it’s also a testable hypothesis. The four white boxes break the problem into smaller parts, and each is a separate issue that doesn’t overlap with any other. In other words, the four boxes together should be a complete map of all the root causes of this problem.

Going deeper, your issue tree could expand like this:

Breaking a large, nebulous problem into smaller parts like this makes it much easier to solve. This will also let us focus on the highest value tasks first. And what are those? 

• Limiting beliefs: This coach has some unhelpful beliefs about what he’s worth, and about making sales calls. 
• Lack of focus: Our coach seems to be trying to do too much—generating leads by phone, email and Instagram. It’s possible to do all these well, but if none of these marketing channels is delivering leads, it makes sense to laser-focus on just one until you create a reliable system that works.
• Wasting resources: We know that activity does not equal effectiveness. It’s possible for a coach to generate hordes of leads, and have them convert into clients at a high rate, but if the pipeline is filled with less-than-ideal clients, you won’t enjoy your work, build your personal brand or see high-quality referrals. 

Step 3: Develop an action plan. Which bucket of issues is most pressing? Nine times out of 10, the greatest gains come from a change in mindset. The limit to any business is the leader, and until these limiting beliefs are addressed, problems will persist. Perhaps he should hire a coach of his own?

Many coach schools also say that the No. 1 determinant of a coach’s success is to own a niche. This coach should get clear on his ideal client and not work with anyone else.

Now, create a list of concrete actions you can take, then start implementing them one at a time.

Strategy 3: Fishbone Diagrams

The scenario: You’re Elon Musk and it’s Aug. 4, 2008. Your third Falcon 1 rocket just crashed into the ocean.

The problem: SpaceX needs to demonstrate the viability of its rocket technology to secure crucial new investment, but only has cash for one more launch. The previous three launches failed. This fourth launch has to work. 

The problem-solving strategy: The fishbone diagram

Also called the Ishikawa diagram, after its creator, this problem-solving strategy has been used since the 1960s by companies like Toyota and Mazda not only to root out product defects, but also to invent new blockbuster products. It’s used within lean manufacturing, Six Sigma, and other techniques. 

How it works: 

A fishbone diagram visually organizes a problem so you can see its root causes. Like the issue tree, it’s a structured way of thinking that aims to leave no stones unturned. It looks like a fish skeleton, hence the name:

I use Miro’s handy template to create fishbone diagrams using a free account. Note: I have no idea if SpaceX used this strategy to understand its problem; this is for illustration purposes only.

Step 1: Clearly define the problem. Here, SpaceX has an obvious but complex problem: its expensive rockets aren’t making it safely to space. 

Step 2: Group causes of the problem into categories. Normally, we want at least two, but no more than six categories. Appropriate here are the 5 M’s of manufacturing here: Man (people), Machine, Material, Method, Measurement.

Step 3: Identify specific causes of the problem.

The first Falcon 1 rocket crashed because a fuel line leak caused a fire. The post-mortem showed that a single nut failed because of corrosion from saltwater. Terrible luck. This falls into the materials category.

The second, redesigned rocket used stainless steel instead of aluminum nuts to avoid corrosion, and upgraded software (measurement). The launch started well, but to vastly oversimplify, the bottom half of the rocket was spinning quicker than expected (a problem of methods), and the liquid oxygen fuel was splashing around too much (a problem of the design of the machine), and the rocket plummeted back to earth.

The next rocket performed almost flawlessly, except that the two stages bumped each other during separation—this time because the halves separated too soon. A delay of one or two seconds could have ensured success (methods, again).

Here’s what Musk’s basic fishbone might have looked like:

Step 4: Plan and implement solutions. The SpaceX team looks at all root causes of previous failures and determines that only a simple timing delay would be necessary. In reality, they were right: Falcon 1’s fourth flight became a triumphant milestone in spaceflight history and a $74 billion-dollar company.

Strategy 4: OOC/EMR

The scenario: You are employed full time at the bank and also have a side hustle: an e-commerce store that sells retro video game systems.

The problem: Essentially, should I quit my day job? You’re bored to tears of cashing checks day in and day out, and know your 9-to-5 days are numbered. But you also like the lifestyle that your salary pays for: weekly dinner and drinks… lease payments on your Audi… the waterfront condo. Can you make the leap with minimal austerity measures?

The problem-solving strategy: OOC/EMR.

It’s a cumbersome acronym developed by Tony Robbins, but this strategy’s effectiveness is unquestionable. It stands for:

O: Get clear on your outcomes

O: Know your options

C: Assess possible consequences

E: Evaluate your options

M: Mitigate the damage

R: Resolve to act on your chosen option

How it works: 

Sometimes a problem is a major life decision, and choosing one path over another can create ripples decades into your future. Choose wisely. Sure, you can check with your gut or ask friends, but a systematic approach wins every time. 

Step 1: Get clear on your outcomes. What do you truly want? You decide that: 

• Covering your $1,800 monthly mortgage is non-negotiable; you love your home. 
• Becoming your own boss is a powerful enticement. Each day you love your job less, and ideally want to quit by December 31.
• You would love to maintain your lifestyle, but are willing to tighten your belt when it comes to entertainment and vacations.

Step 2: Know your options. As Tony Robbins says, “Write down all of your options, including those that initially may sound far-fetched. Remember: One option is no choice. Two options is a dilemma. Three options is a choice.” 

• Option 1: Give notice to your employer today; burn the boats.
• Option 2: Resolve to quit no later than December 31, six months from today, and hope for the best.
• Option 3: Maintain your day job until you are consistently generating $3,000 per month from your e-commerce venture, and make up the shortfall from your savings.
• Option 4: Stay at the bank until your business can replace your salary dollar-for-dollar.

Step 3: Assess possible consequences. For every action, there is an equal and opposite reaction. Let’s look at the pros and cons:

• Option 1: Quit today, and you’d enjoy that freedom you’ve been craving. However, you might run out of money in six months, and alienate your bosses—not smart if you ever need to return. 

• Option 2: Hanging out at the bank until the end of the year would help you feel more secure in transitioning full-time to entrepreneurship. It might also make you miserable.

• Option 3: Leaving the bank only when your business can pay you $3,000 monthly feels safe, but you worry it could take another couple of years to get there. You’d have to pass up some exciting business opportunities.

• Option 4: Sticking to the cubicle until your business income matches your salary means your lifestyle wouldn’t suffer at all. It may also mean that you’re stuck with the suit and tie for another decade. 

Step 4: Evaluate your options. 

Now we know our options and their consequences. It’s time to scrutinize them more closely and rank them.

Robbins suggests asking:

• How important (on a scale of 0–10) is each upside/downside in terms of meeting my outcomes?
• What is the probability (0–100%) that the upside/downside will occur?

You immediately eliminate Option 1 (quit today) because you don’t want to leave your team hanging and because you want to leave this bridge unburnt, on the off-chance that you need to return to work (a 25% chance, you estimate).

You also reject Option 4, because it’s far too open-ended. You need a hard deadline to work toward, and you know that building the business you imagine will require your full-time effort sooner rather than later. No risk, no reward.

Feeling comfortable with your decision ranks high on your priority list (8 out of 10), and another six months to prepare, save and work hard on your business will give you that feeling. And you like the external motivation of the December 31 deadline. However, you’re 95% certain you’d have a sizeable hole in your personal budget. Option 2 is problematic but still viable.

Option 3, to transition from job to business only when your business income reaches $3,000 per month is also enticing. It’s important you maintain at least a few of your creature comforts (10 out of 10), and this money, supplemented by your savings, would let you do that. But you know yourself, and fear that an open-ended deadline like this will lead to procrastination and more drudgery at the bank. Avoiding this is a must for you. 

Step 5: Mitigate the damage.

Only options two and three remain. Is there a way to soften the risks in each? Hmm, how could we cover that pesky budget shortfall? Could you get another paying side hustle, perhaps social media marketing? A bartending job? Sure.

And that open-ended deadline—could you close it? What if you said, “OK, I’ll work at the bank for absolutely no longer than 12 months, or until my business pays me $3,000 per month, whichever comes first”? This feels like a great compromise.

Suddenly, because you used this problem-solving tool, you see a fifth option.

Option 5: Work at the bank part time. You’re unsure your boss will agree, but you can only ask. That would pay you $2,000 a month, plus the $1,000 from your retro gaming e-commerce store, and the shortfall you can cover from your savings for at least a year. Plus, there’s no need to wait six to 12 months to get serious about your side hustle.

Step 6: Resolve to act on your chosen option. 

You decide to make a convincing case to your boss tomorrow for part-time work. Your contingency plan is to seek out another part-time job that would let you quit the bank. This would allow you to dedicate 20 additional hours weekly to your business right away, maintain your lifestyle and feel like a decision-making genius. 

Most importantly, it helps you achieve all of your outcomes from Step 1. Good job, hustler.

Problems Never Stop

When you finally get to a place where your problems stop, it means you are dead. Until then, why waste energy trying to sidestep the inevitable? A much better use of your time is to learn some proven, methodical strategies to beat any challenge. Those above are only four among many.

Just know that the best strategy will fail if you adopt the wrong mindset. According to Ken Watanabe, author of the wildly popular children’s-slash-business book, Problem Solving 101, you’ll have a heck of a tough time if you:

1. Feel sorry for yourself, give up, or fear failure.
2. Spend your time criticizing and being negative.
3. Act like a dreamer, with your head in the clouds, never taking action.
4. Execute without stopping to think in a structured way.

I would add that mastering problem-solving requires a growth mindset, the spirit of which Thomas Edison captured perfectly when he said, “I have not failed 10,000 times. I have successfully found 10,000 ways that won’t work.”

Every problem is figure-out-able. But you’ll save yourself a lot of time and grief if you use the “cheat codes” above. Let us know in the comments how it turns out.

Photo by @sasha.azoqa/Twenty20