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How to solve messy problems (Part III)

Messy Problems

Photo by Annie Spratt via Unsplash

Note: If you haven’t had a chance to read Part I and Part II of this series on solving messy problems, I recommend taking a few minutes to do so. I think you’ll find the context helpful. Hopefully it’s a bit inspiring, too.

Is this still a good time?

Be honest: Did you actually read Parts I and II of this series?

If you didn’t, why not?

Are you in the habit of scanning articles and missed the note at the top of the page? (I’m certainly guilty of this)

Maybe you figured you can pick up what you missed as you go? (I definitely do this, too)

Or maybe you’re not sure if you want to commit to this series yet? (Fair enough, most articles are a waste of time)

I don’t mind if you start here, but I think you’ll get a lot more out of this article if you read Part I and Part II of the series first.

But there’s also a broader point:

In a sped-up world, there’s value in slowing down. Instead of scanning 25-50 articles today, try reading 1 or 2 carefully. Re-read sentences. Work to understand what the author means. Pause to reflect on what you’ve learned and how you can apply it to your life.

If you’re too busy right now, make a note and come back to the article later. You’ll get more out of this — and just about everything else in life — if you make the time to really focus on what’s in front of you.

What have we learned so far?

As you’ll recall from Parts I and II, the objective of this series is to outline a simple approach to solving messy problems that you can use throughout your personal and professional life.

I believe the following framework is useful in a wide variety of situations:

Messy Problems | The Pathway to Impact

The big takeaways?

First, when faced with a complicated and unfamiliar situation, structure is your friend. Following a framework is a helpful way to make sure you’re getting the big things right.

Second, most of us spend far too little time defining the context and truly understanding the problem. Instead, we jump right to designing solutions and executing them, which often leads to a variety of unforced errors.

How does this work in practice?

In Part II, we discussed how slowing down to properly define the context (Step 1) and understanding the root causes of the problem (Step 2) can set us up for success.

Here, we’ll discuss how to develop an integrated plan (Step 3), execute the plan (Step 4), and then learn and adapt as needed (Step 5).

For each step, I’ll begin with an example that demonstrates the value of the step. Then, I’ll explain where things tend to go wrong. Finally, I’ll share some thoughts on how you can more thoughtfully approach each step.

Messy Problems | Step 3

Create an integrated solution

Imagine you’re a billionaire philanthropist. Over the last few years, you’ve decided that the public’s lack of trust in institutions — congress, the military, universities, mainstream media, etc. — is a major threat to American democracy.

To understand why trust is declining, you commissioned a research report from a prestigious think-tank. The report says that trust is low because Americans are unaware of the contributions of major institutions or take them for granted.

The solution: You’ve assembled a team of writers to use social media to highlight the positive contributions of a wide range of institutions.

Assuming you’ve accurately diagnosed the problem, how much of an impact is your plan likely to have?

Who else is already working on this problem? Are your efforts duplicative?

Have similar efforts been tried in the past? Are there analogous situations to learn from?

And by the way, did you decide to focus on social media because you founded a major social media company? Would other channels be more effective?

When solving problems, many of us jump on the first promising idea or simply generate a long list of to-dos. To be more effective, we should strive to create holistic plans that incorporate critical capabilities and opportunities to learn as we go.

Where it goes wrong

  • Our solutions don’t align with the causes of the underlying problem. Typically, this occurs because we failed to successfully diagnose the problem. In other cases, though, our passions, commitments, or pride, send us down the wrong path
  • We don’t fully engage key stakeholders
  • We fail to identify and establish the capabilities needed to support our solutions
  • We create a static plan, rather than creating many opportunities to test, learn, and adapt

How to do it better

  1. Identify any constraints that limit which actions can be taken
  2. Understand what’s currently being done to address the problem
  3. Study what’s been done in the past, including what worked, what didn’t, and why. Consider examples from other sectors, geographies, time periods, etc.
  4. Outline the set of actions that you believe will lead to the desired outcomes. Include the capabilities — funding, partnerships, oversight, etc. — required to support the proposed actions. Also include ways to test, learn, and adapt the plan as you go
  5. Review the plan with internal and external stakeholders, and revise as necessary

In the example above, it seems unlikely that using social media alone will convince Americans to trust public institutions. A more thorough examination would almost certainly reveal a rich history of examples and case studies from which to learn.

For example, why not partner with traditional media outlets, schools, employers, retirement communities, and other organizations to showcase the importance of institutions? Further, why not encourage field trips, site visits, and other immersive experiences to create lasting impressions?

Most importantly, this feels like the type of challenge best addressed by a broad coalition of stakeholders. By identifying other individuals and organizations with an interest in preserving American democracy, it’d be possible to develop a much more integrated solution.

Messy Problems | Step 4

Execute in earnest

Imagine a newly-elected Mayor that won by promising to deliver city services more fairly. Trash collection, road repairs, snow removal, and other services would no longer vary by neighborhood. After winning the election, the Mayor enlisted her deputies and a prestigious consultancy to understand why services are not provided equitably and create a plan to fix the problems.

Now consider Tom. Tom holds a senior position in one of the city’s departments. He was occasionally consulted during the planning process, but it was clear that the Mayor’s team and her advisors were in charge.

Just last week, Tom received a copy of the 200-page report from the consultants. He was notified that his team is accountable for implementing several of the recommendations.

How comfortable do you think Tom feels with his responsibilities? Will he be able to translate the report’s recommendations into concrete actions for his team?

A number of the recommendations will undo Tom’s past accomplishments. How invested will he feel in the overall success of the new recommendations?

Simply put, execution is about bringing plans to life. Only through our actions — through execution — can we generate the impact that we seek.

Where it goes wrong

  • We create a thoughtful solution, but no real follow-through occurs. Often, this happens when priorities change, incentives are misaligned, or early results are discouraging
  • We follow-through, but do so poorly. This typically occurs as a result of inadequate capabilities, poor coordination, or insufficient oversight

How to do it better

  1. Invest enough time up front to ensure that you and your stakeholders understand the need for change, share a vision for success, thoroughly understand the problem, and have developed a well thought-out solution
  2. Ensure that the necessary capabilities are put in place, including the appropriate leadership, oversight, and coaching functions to support stakeholders along the journey

When someone “fails” to execute a plan, there are almost always several other failures that occurred somewhere upstream.

In the example above, it shouldn’t be a surprise if Tom decides to withhold his full support for the initiatives. Likewise, he might very well lack the context or capabilities to deliver the desired results. To avoid these types of “failures,” it’s critical to keep execution in mind throughout the entire planning process.

On the other hand, unexpected things happen. As a result, we need mechanisms to adapt as needed. More on this in a moment.

Messy Problems | Step 5

Learn and adapt

Imagine that you recently joined the board of a local non-profit. You’re passionate about the cause, but so far you experience has been frustrating. Meetings run long, tempers boil over, and little seems to be getting done. Somehow, you seem to be the only one that’s noticed.

What are some things that you could do to improve your experience?

What could you have done to avoid getting into this position in the first place?

What advice would you provide to a friend who is also considering joining a board?

In situations with a high degree of ambiguity, complexity, and dependency, there’s a lot that can go wrong. To succeed, it’s imperative to test the things that are uncertain, learn as quickly as possible, and continuously adjust our actions.

Where it goes wrong

  • When developing an integrated solution, we don’t create adequate opportunities to test and learn
  • We avoid honest reflection because of competing priorities, pride, or fear of negative consequences
  • We wait too long to reflect on what we’re learned. In the process, we become overly invested in the current path or opportunities to change disappear
  • We fail to translate lessons learned into different behaviors

How to do it better

  1. Set the expectation that learning and a willingness to adapt are critical to the success of the initiative
  2. Incorporate opportunities to test, learn, and adapt throughout the effort
  3. Create clear processes and roles to ensure that learning and adaptation take place

In the example above, there’s a lot you can do to salvage the situation.

First, remember that your attitudes and beliefs determine how you experience an event. In this case, re-framing the situation as a learning opportunity makes it easier to recognize the successes — for example, seeing what isn’t working — that you might otherwise ignore.

It is also helpful to put formal structures in place to encourage learning and adaptation. In this case, you might ask a peer or mentor to check in with you on a regular basis to assess your progress, help you identify solutions to unexpected problems, and otherwise make the most of your time.

And finally, you can try to avoid situations like this by creating opportunities to test and learn sooner and when the stakes are lower. In this case, you might have volunteered to do a small pro-bono project for the board before deciding to join full-time.

Confronting “failures” and unexpected developments is a necessary part of tacking messy problems. By embracing this reality, we can turn potentially uncomfortable learning experiences into tremendously beneficial opportunities.

Where do we go from here?

That’s it. Five steps — plus some iteration along the way — to help transform an overarching desire for change into tangible impact.

For me, the hardest part is finding the patience to consistently follow the approach. When I take the time to work through each of the steps, good things happen. When I jump ahead to the answer, trouble follows.

So here’s my parting challenge: The next few times a problem seems more complicated or ambiguous than you’d like, try using the approach I’ve laid out here.

If the approach doesn’t feel right to you, no problem. I’m sure you’ll gain a few new insights along the way.

If you find that this approach resonates, keep using it and begin to make it your own.

As I said in Part I, the world desperately needs more problem-solvers. Hopefully this series has inspired you to finally tackle those messy problems you’ve been meaning to solve.

Note: A version of this article was previously published on