It’s easy to tell when someone is working, but how can you tell when they’re making progress? Simple work, like mowing a lawn or washing a car has transparent progress: as each small unit of work is completed it’s visible to everyone. But with complex work, building software, running a business, writing a novel, it is harder to identify true progress. Some of the work will require thinking and exploration which may go on for hours or days before there are visible results. Other work may involve so many different sub-tasks or conversations with others that there’s no way to know how efficiently the work is being done, or if the effort expended is paying off at all. Challenging work, or work with large numbers of people, always makes it harder to separate work from progress.

As a result, people in power on challenging projects often feel insecure about how things are going and rely on misguided measures, like how many hours their employees work. The flaw is that hours of work, and measures like it, are an input: they says little about the output, and productive a person is with those hours. Most common measures of productivity are flawed in the same way.

Why progress is subjective

The first big challenge with progress is admitting that it’s subjective. There is no universal ideal of progress that you can use to judge whether things are improving or not. One project might be to dig a hole in the ground, while another might be to fill one in. The removal of dirt can be progress or a setback depending on what the purpose of the work is supposed to be. The more challenging the project, the easier it is to get lost in pockets where the true goal has been forgotten.

Giving people the tools to recognize when they’re wasting their time is one of the biggest responsibilities leaders have. A leader has to define a collective sense of progress that incorporates everyone’s contributions into a meaningful whole and strike a balance between something tangible enough for individual contributors to relate to, but broad enough to define a strategy for the team, organization or company. Standing on a desk and saying “Let’s do great work and work hard!” may momentarily energize people, but it’s just a sentiment and you can’t organize work around sentiments. It must be converted into tangible directives that people can follow. What does good mean? What kinds of things?

What leaders can do to define progress

There’s two parts to defining progress. The first is in planning the work and outlining a set of goals the work is supposed to achieve. If I told you to put out the trash, and pointed you to 3 full trash cans and a street with a signpost that said “put trash cans here”, it’d be clear to you what progress looked like. Even with complex work, the goal of a leader is the same: you want everyone to know how the world should be like when they’re done. Then they can compare what they’re doing today with the goal and make adjustments. This vision of completion can change, but everyone’s vision should change together (and it’s the leaders job to make that happen). If there is no vision, the first goal leaders set can be for everyone to contribute ideas for the vision.

Much has been written about this process, often called goal setting, vision, project or release planning. Some techniques focus on flexibility and short term cycles (e.g. Agile development for software), others on big long term plans (e.g. constructing stadiums or skyscrapers). There is no one perfect method, and it’s wise to pick a method based on the project at hand.

The second, but most often forgotten, part is the daily guidance of a team towards progress. It’s the leader’s job to continually reflect back to individuals how their work fits into the goals. In every meeting, discussion and e-mail the leader must reinforce, remind, cajole, and motivate people’s work towards whatever the collective goals are, flagging work that is questionable and activities that are unnecessary. The leader has the best perspective on the entire project and he must share that view as often as possible. He is in the best position to see when people are going the wrong way, or worse, disrupting other’s progress towards the goals. And if he communicates what he sees clearly enough, even if he doesn’t have all the answers, other people will ingest and apply that view themselves, adjusting their work to maximize progress.

Common work measurements (Easy to measure / Limited value)

The flippant response to worries about progress is to start measuring things. The belief is that by breaking down progress into metrics you give people focusing tools. But this often backfires: people work to the metrics, not the goals.

I’ve seen organizations that measure things like:

• How many hours you were in the office
• Number of reports, specifications written
• Presentations given
• Calls made
• Lines of code written
• Number of bugs fixed
• E-mails sent

All of these are poor measurements, since they only capture activity. Fixing more bugs on a given day may mean that you only chose easy ones to work on. Lines of code measures only verbosity, not quality. All measurements have loopholes that can be exploited. But since it’s so easy to measure these things, it’s common to see them. They can help a manager, but only if they are interpreted carefully, used in conjunction with other information.

Common progress measurements (Harder to measure / High value)

There are ways to measure progress but they’re very subjective are require more thought on the leader’s part. These questions force some thought and dialog about the work in question, which is good.

Measuring a unit of work:

• This unit of work contributes to which goal(s)?
• How does it help us get closer to that goal?
• How large a contribution is it? (Does it get us 5% closer to the goal? 50%?)
• Is quality sufficiently high?
• What other units of needed work does it support or enable?

This works no matter what the goals are. If your goals are vague, such as “experiment with new uses for mashed potatoes”, time spent bathing or wallpapering with mashed potatoes counts as progress. If the goals are directed, but not specific, as in “Make the database more reliable”, there’s room for people to be creative, but there’s a clearly defined direction for evaluating progress. But if you define the goals too tightly (“Make the text blue”) we’re back to mowing lawns and taking out the trash: you’ll only get a very narrow kind of progress. Finding the right level of detail for goals is a craft and it takes experience to get it right. Typically you want to create a hierarchy of inherited goals with increasing tightness: some for the entire project, some for each sub-team, and some for each individual person.

Measuring individual progress:

• How much closer did your work today get us to finishing the project?
• Does the quality level of your work match what we need?
• How many people on the team have you positively influenced?
• What challenges did you overcome?
• What challenges did you prevent from ever happening?
• What difficult, but essential, questions did you ask that others forgot?
• How did you make us more efficient towards our goals today?
• What roadblocks are you currently facing that prevent faster progress?

Measuring team progress:

• How much closer are we to fulfilling our goals?
• How close are we to the needed levels of quality?
• What unaddressed problems are slowing us down?
• Is our remaining schedule accurate? What would make it more so?

As a manager, whenever I’d stop by someone’s office and say “How’s it going?” it was often these questions of individual and team progress that I was trying to get at. When I did my job well I’d spend much of the day in conversations about these things, or in arguments trying to get conversations to focus on these things.

The work to progress ratios (Inefficiency of creative work)

So far I’ve narrowly defined work and progress in linear terms: you’re at point A and need to go in one direction until you hit point B. That’s nice and simple but I’ve never worked on a project that went in a straight line. Complex and creative work just doesn’t happen that way.

The more challenging the problems the less linear the work will be. If you’re trying to cure cancer or build a new kind software you will be forced to find new ways to do things, or to make new combinations of existing ideas. This demands that many attempts will be made that are unsuccessful. You’ll need to try different designs and explore many alternatives, learning as you go, to find satisfactory solutions to your toughest problems. This is fact: there is no linear path through big challenges, it’s a process of exploration and experimentation. Creative work is by definition not efficient: you have to explore and experiment to make progress.

This doesn’t mean that separating work from progress is impossible. Instead it means that leaders need to set expectations for which goals will require high ratios of work to Progress (W / P). Leaders can help people isolate the tasks that will require many attempts to get right (designing a new architecture), from those that should be straightforward (data entry).

The work to progress ratio expresses how many units of work/time are required for each unit of progress. For example:

• Taking out the trash, Data entry: 1 to 1
• Designing a new search algorithm: 5 to 1.
• Redesigning the entire user interface: 5 to 1.
• Creating a perpetual motion machine: Infinity to 1.

And to help people make sure they’re keeping their ratios as low as possible, ask these questions after each unit of work:

• What did we learn from this unit of work that can help with the next unit?
• Do we have new questions for the next unit of work that will increase the amount of progress?
• Is there more information we need that will make the next attempt better?
• Is there a better way to define the goal?

The work to progress ratio implies other things: A more skilled or intelligent worker can achieve a better ratio than a less skilled one.

It also implies that different levels of quality require different costs. It might take 5 attempts to find a mediocre solution to a problem, but 15 to find an excellent solution. Part of the leader’s work is helping the team to determine which investment is appropriate for which goals.

The last word: the hard core psychology

Underneath all of this is an important psychological element. Even when you know the optimal way to make progress, you have to choose, or get your team to choose, to go and do it. This is not an intellectual challenge: it’s psychological. Knowing what to do, and wanting to do it are too different things. There is no universal law that says that best way to achieve progress will be the most fun. At a certain point it’s no longer a question of planning or thinking: it’s a simple choice that you, me, or anyone has to choose to make: will I do what I know is the right thing, even if I don’t want to do it, don’t like to do it, or am afraid to do it?

The burden of answering this question falls back on leaders. They face the same questions in their own work, and their answers will set the tone for the rest of the team. If they demonstrate doing the right thing, even when it’s unpleasant or not as fun as other work, others will follow. The ideal work environment is one that has a strong culture around being hard core when it comes to doing the right thing. People should be rewarded, by their leaders and peers, when they make the right choice.

Acknowledgements

This essay was inspired in part by a conversation with Paolo Malabuyo.

References

• Taylorism: As a general reference, Frederick Taylor created a theory of management about optimizing human performance. It focused on assembly line and manual labor tasks.
• Productivity: often defined in economic terms, productivity is one way to measure how efficient an organization is in getting work done. But the core word, productive, usually implies the measurement of work, not progress.
• Various definitions of progress. Wikipedia’s list of topics related to progress.

[Edited for clarity & concision: 6-20-2017]