Choosing the Right Opportunities

A critical decision every organization needs to make is choosing the work we will do. Choosing one work item over another is in many ways similar to other investment decisions. As in other investments, we cannot pursue all available opportunities as we do not have enough time, capital or people to divert to each one of them. Hence we need to prioritize the investment opportunities knowing that choosing some means saying no to all the other.

A typical prioritization system will stack a series of options, the things on which we could work, ranked by its potential to generate the value we want as an organization. Assessing the priority we should give to each option is not a trivial task, and many different techniques have been used, typically involving the definition of a scoring card balancing aspects such as organizational strategic alignment, potential financial value measured (for example net present value, NPV, or return on investment, ROI) and risk profile, etcetera.

Donald Reinertsen has described the benefits of using the weighted shortest job first (WSJF), weighting by cost of delay (COD). This prioritization method has amongst many other advantages its dynamic approach. It is based on comparing the cost of not taking each option now, hence delaying it by a unit of time and looking at how much will we lose. More formally, it is the partial derivative of the total expected value with respect to time. One more useful way to look at it is thinking of the total value of the option as a water tank that has a leak and hence the total amount of water in the tank (total value) decreases over time. The longer the time we wait the less water in the tank. How fast it decreases depends on the size of the leak, which is the COD.

This dynamic aspect of cost of delay is what, in my opinion, gives this method an enormous advantage over other simpler approaches, like looking statically at the total ROI. On the negative side is the difficulty of estimating COD, but I must say I did not find it normally harder than estimating NPV or ROI. Learning the art and craft of estimating COD and hence prioritizing our portfolio is a long, arduous but absolutely worthy endeavor. It is learning to see how value evolves over time.

This post is part of a series on planning. In the same series, you can also read:


The Timing of Planning

Considering the amount of uncertainty increases the longer into the future we try to see, planning once and then executing following our plan does not look like a winning strategy, no matter how much effort we put into planning. We may even be hurting the quality of our planning by doing too much of it at the onset.

What is a planner to do, then? We can spend just enough effort at the beginning planning our endeavor. Then start executing, and refine our understanding with periodic review of our progress and again spending just enough effort to (re)plan our work ahead. “Just enough” is a problematic expression.

How will we know how much is just enough initial planning? I don’t have a satisfying answer yet, but practice has led me to some heuristics I keep refining: If you are still uncovering risks and opportunities that you did not see before, that have the potential to alter your chances of success and which outcomes can be influenced by mitigation or preparedness of any kind, you ought to keep planning. When the risks or opportunities you uncovered had been trivial enough, then it is time to stop. If you have started running in circles, chasing “unknowables”, or pretending you know things you cannot know, it is also time to stop planning. Start with a not so large effort and then progress your initial planning in short loops, when the improvement done over previous cycle does not feel significant, and we still feel we put enough effort and made wise choices, it is time to stop.

Another difficult decision is how often should we review and replan. Again some rules of thumb may help us decide. The farther ahead we can see the longer we can keep our heads down busy with execution without planning again, and more effort we can put in each round of planning. In risky circumstances, unknown terrain or in the presence of unpredictable events we will be wise to plan often, looking ahead to a shorter time horizon, and spending less time doing so for each loop. Each loop should be firmly grounded in reality, considering all feedback we can get from our execution and the events unfolding around us.

No standard planning approach is universally adequate. The answers to when, for how long and how often to plan are highly contextual, and you ought to make a conscious choice. We are all called to lead our organizations making a explicit decision that is grounded in our context and then constantly refinining our approach to this timing questions as get more and more feedback from reality.

This post is part of a series on planning. In the same series, you can also read:

The Outcome of Planning

“To plan” is much more important than “the plan”. The outcome of planning is not a document, but the things we learned about our current state, goals and impediments; the preparations we made for a possible future in which some uncertain events happen; and the actions we took to get ready for action.

When, after ardous preparations, our plans look like long to-do lists, with the expected duration attached to each task, and an assumption that the future will unfold as the unimpeded delivery of item after item in perfect succession, we are just fooling ourselves and reducing our chances of success.

When we skip planning altogether because the future is uncertain, and we abandon any expectation of being prepared for risks we can foresee but not predict, we are choosing to reduce our chances of success too.

The ultimate aim of planning is increasing our chances of success with a relatively small effort investment. Abandoning after planning is also a form of success, as it costed us little to avoid a likely failure. Avoiding impossible endeavors is only one of the flavors in which successful abandoning comes. Another often overlooked flavor is to complete something doable, but which benefit is not worth the effort. Beware.

Planning, Forecasting and Committing

Plans are not commitments. If I can commit to a plan, it is a very bad one. If I want to commit to a plan I created before starting, I am accepting I will not learn anything useful during the journey, that is, by actually doing the work. I am not yet ready to accept that, are you?

A plan is the result of planning. Planning, the act, is the important thing. When planning we often detail what it would look like when we achieve what we want, what needs done, the methods by which we can make it happen, the risks and opportunities involved, mitigation and possible courses of action to respond to those foreseeable circumstances. A plan is not an end date, a work breakdown or a rigid course of action, but it can contain some of those things and even multiple variants of them depending on factors unknown or unknowable before we start.

Reassessing our plan regularly as we go is a wise thing to do, even more so when we cannot reach our destination using a well-known, repeatable, and predictable path. We can call that approach progressive or adaptive planning. If nothing new is discovered since last assessment we just keep course with the previous version of the plan, only a bit further along the journey. Often we will need to adapt our plan to accommodate some discoveries as reality unfolds. Possibly, we discover something so different to what we expected than the previous plan does not make sense anymore and we create a new one from scratch. In some cases we may discover our objective is not reachable or it is no longer desirable and we abandon the objective altogether. In short, plans change along the way.

Then, what is it that I can commit to? I believe the answer is more nuanced that never committing or commit to any plan that you create. Business requires some predictability in due dates, quality we can trust or actual cost close enough to our estimates. In order to take a responsible approach to committing, we need to forecast. We use the hard won knowledge we acquired through planning to forecast a set (not one) of foreseeable end results for that variable and their associated uncertainties.

To commit I have to answer a very difficult question: how likely is it that I deliver on the expected result or better? The context will also help me understand how much risk is acceptable in my commitment. Often we have to commit to something under most or all currently foreseeable circumstances. That is industrial-strength likelihood. Hence, the most likely result is not the answer. Instead we should commit to what we can deliver in most foreseeable scenarios, even in the bad ones. Most of the times that does not include unprecedented earthquakes, unforeseen disasters or great new technologies that will reduce the required effort to a tenth, but the ones we can expect. Of course, if I am planning in times of COVID-19, that is at the time of writing this, and I am not including contingencies for outbreaks and other disruptions created by the pandemic, I am being foolish.

When the unexpect-able happens, the black swan, our commitment will not hold. But that is a different story.

Hiring for Strengths or Lack of Weaknesses

Should we hire for the strengths we need even though other aspects of the candidate should be a bit rough or for well-rounded difficult to blame candidates with no visible weaknesses and no visible world-class talents? You may think that is not an easy choice that requires careful consideration but you may have already decided implicitly when you have chosen who is interviewing candidates and who will participate in the decision.

When we get hiring decisions taken by a committee we will inevitable end up with the most difficult candidate to knock out being chosen. He is the candidate with less obvious weaknesses. That does not guarantee that he can do anything exceptionally well.

When a single person is interviewing personal biases play a too prominent role. We risk choosing for proxy attributes that are easily observable, being taken as signal of specific strenghts. Exagerating to make the point, male middle-age white candidates present proxy attributes that can be confused for talent proxies and that guarantee no success.

The middle ground? It could be a diverse interview panel which role is to provide input to the decision but not to decide and an individual decision maker. That helps balancing individual biases and our search for exceptional talent, even with some rough edges.

Appreciating Appreciation

I have often failed to show enough appreciation for our people and their contributions to our organization’s successes. Appreciation’s virtues do not stop with justice, but they also include fostering better attitudes in the appreciating and appreciated parties. Appreciative organizations produce better outcomes generally. Honest appreciation is a safe thing, with no counterindications. I shall do more of it.

Vision and Storytelling

Before asking me to work hard to change what I do, I need you to show me how things are going to be better. Help me connect emotionally with the better future we are building. Tell me the story of how we improved people’s lifes, how we overcame the obstacles and made it happen together, as if it had already happened. Energize me. Only then I will be ready to discuss what exactly I need to change, how much effort will be needed, how do we engage others and when will we do it. Then we would be discussing the details of a shared goal.

I know it is not an easy thing to do. Even though I know I need others to help me engage emotionally with the cause before I can contribute, I sometimes skip helping others connect. I typically tell myself this time it is obvious and we all know why we need to do it. This time I don’t need to go through the tough emotional labor of connecting us all to what is possible. They will just engage, won’t they? I inevitably feel silly when they don’t, and I realize I just did it again.

Why is such a hard thing for me? It requires 3 difficult things. First I need to be vulnerable, showing my own emotions and connection before I can connect with other’s. If that was not enough, it requires me listening at a deep level to understand what makes others tick which I may have not even considered. And finally, it will only work after accepting that it is our common connection that defines the shared goal, and as such I don’t get to define it.

Sometimes I did just that, and it was beautiful. I shall do more of it.

Improving and Solving

Continuous improvement and problem solving are related but not the same, more like cousins than twins. Both are useful skills that help us succeed as an organization. I believe the main difference is in our outlook: are we aiming at moving to a better place or recovering our balance?

Problem solving is regressive: we were good, then something happened and now we have a problem, so we should fix it to return to a good state. Continuous improvement is progressive: we are here but we want to be there, so we should take on a challenge that will take us closer. They require and reinforce different mindsets and attitudes. Solving implies there is a correct solution, improving implies taking any of the possibilities that will make it better.

Better for what? Continuous improvement is not possible without a vision that describes the meaning of better, that is, where we are going towards. Unlike in other problem solving exercises, in continuous improvent the challenges we undertake are defined by and chosen because of their contribution to the gap between our current situation and our desired destination. We don’t need to be in trouble today, we are not where we want to be. The quality of the solution to such a challenge is measured not only by how much closer it will make us to our vision today, but by how much it will ease the next steps in reducing the gap tomorrow.

Are you solving problems to get back to good or improving towards better? Is there an “improvements this way” sign telling your team where to go?

Positive Direction This Way

Understanding Before Solving

When trying to solve any problem, the biggest risk is jumping to solutions before framing the problem effectively. Most of the times a solution comes to mind it is too early to think on solutions. Instead stay focused on the problem, can you fully describe what is happening as observable facts?

My brain works best finding obvious solutions to evident problems very fast, and it keeps trying to execute this over and over again, as if to show off its best trick. I often feel compelled to ignore all non-evident problems and non-obvious solutions and find a quick match. What is even more concerning to me is that I often feel rewarded for doing so. The behavior I see in many people seems to be consistent with my own. I don’t know what motivates people thinking processes or how they work and I am not aiming at a general theory. Instead I am just recording an observation: many of us act often in a way that appears similar to mine from my limited vantage point.

Here it is a practical suggestion that may help you avoid this pitfal: when you feel you already comprehended your problem and can detail the causes and effects at play, then look for parts of the bigger system not yet visible to you and their impact on the problem with which you are concerned. If you cannot see any new interactions keep watching, you have not learned to see yet. You are only done when you can see plenty additional interactions but they do not alter your understanding of the behavior of the system, instead the new interactions are sources of nuance and detail within the network of cause and effect relationships that shapes the system behavior. Then rest for a second, congratulating yourself on having tamed your inner impacient know-it-all, and get back to work because now it is time to start acting on the system: what can we do to see if our understanding holds itself?

Mindful Practice vs Best Practices

I felt Gil Broza really touched down lately on an important aspect in Why exactly mindset matters more than practices: anything you do, any practice, can be done in a shallow way and achieve nothing. You can go through the motions like a template zombie, and you also have the option of addressing the real need, aiming for the real goal.
We all know you cannot think your way into a new way acting, so we need deliberate practice to guide us into the new thinking. There is a chasm between adopting best practices as ready made templates, that will work because… well… they are the best, and adopting a mindful practice attitude, as in golf, guitar, knitting… practice. Getting a thing you can use versus doing to learn. It is not the template that matters, but being mindful about what we are trying to do and having a way to say whether it is working or not.
Good practices are contextual, and in the right application context they can be very useful. I believe mindful practice is as close as it gets to a universal principle for skill acquisition.
What are you trying to achieve with each of your current practices? Who are they for? What are they for? How do you know they are working?