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  • Writer's pictureJoey Savoie

Problem-Solving in Five Steps

When you found a charity, problems are inevitably going to come up. It could be that a donor you were counting on does not fund the project, a key employee leaves the job, or a government agency requires a document you have never heard of. Underneath the shiny website and carefully branded social media pages, most organizations have a consistent stream of diverse and novel problems. A big part of being a well-rounded and talented charity founder is the ability to solve these novel problems effectively. Hundreds of skills and heuristics can lead to better problem-solving: this article covers five of them.

​What to do when a problem is detected:

  1. Determine how important the problem is

  2. Generate solutions

  3. Compare solutions

  4. Implement solutions

  5. Upstream problem-solving


Whenever a problem is detected, the first step is determining how important it is. There will always be more problems than time to solve them. As such, you have to prioritize how much time and even which problems to solve. Maybe your computer mic is broken and you have to find headphones every time you Skype. Irritating, but hardly an important problem if your organization just got information it might not be having an impact.

The more important the problem, the sooner you should get round to it and the more time you should dedicate to solving it. Often it’s worth putting more time into problem-solving than your intuition suggests, as problems get bigger when ignored. (Check out our productivity chapter for an additional framework on identifying high-impact tasks.)


Every problem has a solution. In fact, every problem has multiple solutions. For each problem, you should try to generate a number of solutions. You don’t want to give up on a problem without coming up with and attempting multiple solutions.

Often solutions will come to mind quickly, but sometimes it might take some out-of-the-box thinking. Say you’re trying to figure out what to do with an underperforming employee. Maybe a couple of ideas come up right away: a) You could fire the employee. b) You could ignore the problem. c) You could do a performance review on the employee and help them work through the issues. These might seem like decent solutions but dig a little deeper and far more come up.

One way to generate more options is to look at the problem from different perspectives. For example, you could frame the problem in a different way. “Why is this employee underperforming” might lead to some solutions you have already thought of. Well, maybe they hate the whole workplace and are going to move on soon in any case, thus voiding the problem. But it can also generate other possibilities. Maybe the employee is underperforming because they do not like their manager, so maybe the problem could be solved by moving them under a different manager – this is a new solution that could be helpful.

Another way to look at the problem from different perspectives is to ask others, particularly if you combine strategies and use different framings of the problem when asking them. Everyone comes at problems a little bit differently, so one of the big advantages of having a strong advisory board is to come to them with problems and see if they have different solutions. Sometimes it will come from thinking differently: “Is the employee missing a key skill you assumed they had? Maybe they are underperforming due to a lack of training.” Other times it might come from just having different information: “Maybe you should tell the employee to apply for X new job I know about – it seems like a good fit for their skill sets.”

After you have a solid list of possible solutions, you can move to comparing solutions.


How much time to spend comparing solutions depends on the magnitude of problem-solving. But keep in mind that generating and comparing ideas is likely worth 10% of the time the solution will take to implement. When comparing solutions, make a comparison spreadsheet or a simple pros and cons list. Remember that solutions are not exclusive – your plan might involve trying one low-cost solution first then implementing another if that doesn't work. By the end of your comparison, you should feel comfortable talking to an advisor or trusted friend (and often this is a good thing to do) about the options you considered and why you came to the solution you chose.


The first step in implementing a solution is communicating the plan clearly to everyone it involves. In some cases this might be no one, but in most cases you will have to explain to your team why you have gone with this plan (good thing you have practice from when you explained your solution to your friend). The solution is best presented clearly, assertively and confidently.

You do not need to always be confident you have made the right call – everyone makes mistakes. But if you are confident in your process you can confidently say “I think this is the best call on it given the time I was able to put into it”. Many solutions require habit-forming. There are great resources on how to do this, including the book Atomic Habits. Many require changing your team’s mind on key issues (the best book on this is Switch). This can take time and patience. Most of the time a solution will not be universally liked by everyone, but over time and with encouragement, people will adapt. For example, say you are getting your team to switch to a new task management system. You might plan to speak about it at a meeting your team has regularly. Start with the “need”, or why this is happening. “As you all know, our team has been struggling to stay on top of all the work we need to do. A few important things have fallen through the cracks.” Next, you want to briefly explain your process in coming to the solution, drawing the person along on the journey you went through. “I talked to a few other organizations and spent some time researching possible solutions. One thing that came up was the type and way our task management system is used. I compared about a dozen task management systems and it seems as though quite a few of them would give our team big benefits.” Finally, explain the transition and implementation of the idea. Often small steps are good. “We are going to try this new system for a week with our communications team and re-evaluate after that. If it seems to help some of our problems, we will switch everyone over.” To help ease the change, document the new processes by writing standard operating procedures: this way everyone is on the same page about how things should be done. Acknowledge possible flaws or complaints but be reassuring and firm and remind them of the benefit (partially the long term benefits). “I know it will be a pain to move all our old tasks over, but once we transition we will get more done every week. And the more we can do with our limited resources, the better we can achieve our goals as an organization and save lives.” At this point, you might think your problem is solved and you can move on. But you can’t quite yet.


The last step is solving the problem upstream. Solving problems can be categorized in two ways: upstream problem-solving and firefighting. So far the process we have talked about is mostly firefighting steps. ​

Upstream problem-solving refers to actions that can be done to prevent problems from arising,

like getting a flu vaccination to lower your chances of getting the flu. Firefighting, on the other hand, refers to reactive actions taken after the problem occurs, like going to a doctor after you feel ill. Most often an ounce of prevention is worth a pound of cure, and the more problems you can solve upstream the easier it will be to fight the (still inevitable) problems that come up downstream. Often you have to experience the flu to know the importance of preventing it the next time. For every problem you solve, you should think: “Does this have a chance of coming up again? How can I prevent this sort of problem from reoccurring?” A lot of upstream problem-solving comes from the realization of recurrent patterns and the seeing of problems as “another one of those” instead of a unique situation. Of course, each situation is somewhat unique but that does not mean the same underlying problem can be causing it. For example, say you are looking at three problems on your desk. One is that your operations team is falling behind on their monthly bookkeeping. The second is a promising new idea that you would love to pursue, but you don’t have any staff to spare for it. The third is that your communications team is not responding well to emails sent to your website; many of them seem to fall through the cracks. These may seem like unrelated problems in unconnected departments, but they could also be a sign you have not built in enough organizational slack to deal with a changing and dynamic workload. A firefighting solution might be to pull an all-nighter responding to the emails and doing the bookkeeping. An upstream solution might be to hire more staff or narrow the scope of your project, freeing up organizational time. Upstream problem-solving does not come naturally. It’s not trained in school and not practiced in most workplaces. There are few resources aimed at teaching upstream problem-solving, but Upstream by Dan Heath is a deep guide both to the barriers – i.e. the mindset that a problem is unavoidable, “not my problem”, or can’t be dealt with right now – and to some solutions. Key questions to ask in upstream problem-solving are:

  • How do we bring together the right people?

  • How can we change flawed systems?

  • What’s the leverage point?

  • How can we spot problems before they happen, steering clear of false positives (e.g. a screening test incorrectly shows that someone has cancer)?

  • What does success look like and how do we avoid “ghost victories” (i.e. failures in the trappings of success)?

  • How do we avoid causing harm in flow-through effects?

  • As nothing happens, who foots the bill?

More materials including a summary and the first chapter of the book are available on the author’s website.


When a problem is detected, you want to:

  1. Determine how important the problem is - Either dedicate time and energy to it or deprioritize it accordingly.

  2. Generate solutions - Use tricks like reframing the question or ask people with different ways of viewing things, or for best results use both.

  3. Compare solutions - Use a simple pros and cons list or a more complex spreadsheet to evaluate the options you come up with.

  4. Implement solutions - Communicate clearly and firmly the process and solution you came to and set up organizational habits to ensure the solution happens long term.

  5. Upstream problem-solving - Consider the cause or origin of the problem and how your organization could prevent future problems of the same type.


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