Time isn’t the only way to plan and estimate

Consider milestones, attention, and energy too

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Source: this are.na block

Time.

I often use time to plan. And estimate effort.

“They’re spending 20 hours/week on X project and 20 hours/week on Y.”

“Fixing this bug would take them about 8 hours.”

“Getting to our MVP will take 3 months to ship.”

Sometimes, I feel silly about using time to estimate. Particularly when we’re trying to estimate work that isn’t as defined. It’s hard to know exactly how long it will take to scope, test, design, test, build, test, and launch a new product. We don’t know what the scope is. We might find out in testing that the scope needs to change. In dev, we might find out our design needs to change a bit.

Of course, time can be a useful goal. I try to get eight hours of sleep at night. I try to have two hours of uninterrupted focus time Mondays through Thursdays.

Time can also be an enabling constraint. A fixed launch date is a great forcing function for prioritization. “We can deprioritize features that aren’t as important, we just can’t move this deadline.”

But I can’t help but think that thinking in time holds us back sometimes.

Why do we default to thinking in time? It’s the primary way we plan and estimate effort. It’s how we determine how much we charge. It’s how we know when to bring developers into a project. It’s how we know when things happen. Everyone knows what time is. It’s legible. Universally understood. This is why we default to thinking in time.

I wonder if there are less legible — but intuitive, hopefully — ways of planning and estimating effort. I want us to explore three: milestones, attention, and energy.

Milestones

A major milestone in Breath of the Wild: getting the Master Sword!

My girlfriend was sharing with me how time management is less a thing in the Philippines:

There is no concept of time management in the Philippines. If you try to Westernize your day by estimating when you’ll be in certain places, you’ll disappoint yourself. Time operates differently there.

This tracks with my experience visiting the Philippines. When I'm there, I’m late to everything (and so is everyone else). I’m less meticulous about planning my schedule. Because, as my girlfriend said, I’m not likely to meet it.

I like the distinction between Chronos time and Kairos time. In The Consultant Out of Time, Tom Critchlow summarizes (emphasis mine):

Clock time is what the Greeks called Chronos - fixed, measurable, predictable time. Living in clock time is about carving time into fixed units. Employees inside organizations operate on clock time.

Narrative time is what the Greeks called Kairos - time moves when something happens. Living in narrative time is about carving time into events. Indie consultants operate on narrative time.

When we’re on Chronos time, we’re on the clock.

When we’re on Kairos time, we’re on a journey.

There’s something here that helps me better understand how we estimate effort on work that isn’t well-defined.

A Kairos way of measuring effort might mean estimating based on events we intend to get to rather than deadlines. I’m calling these events milestones. Each project is a series of milestones we’re aiming to get toward, together. The project is the narrative. Each chapter is a milestone. We're writing this story together.

When I used to consult on organizational transformation efforts, I was always asked about our timeline. I’d share milestones-first timelines, to help our client understand that we want to achieve milestones, rather than go through the motions on specific dates:

• Milestone 1: organizational challenges understood (3 weeks)

• Milestone 2: six experiments collectively ideated (1 week)

• Milestone 3: three pilot experiments prioritized and resourced (1-2 weeks)

• Milestone 4: three pilot experiments retrospected (6-8 weeks from Milestone 3)

• Milestone 5: second cohort of new experiments scoped, prioritized, and resourced (1-2 weeks from Milestone 4)

• Milestone 6: second cohort of new experiments retrospected (6-8 weeks from Milestone 5)

The milestone is shared before the time length:

• Milestone 1: organizational challenges understood (3 weeks)

I avoided sharing the time length before the milestone, like this:

• Week 1-3: organizational challenges understood

• Week 4: six experiments collectively ideated

• Week 5 / Week 6: three pilot experiments prioritized and resourced

• …

• Week 20: second cohort of new experiments retrospected

This easily sets up the expectation that, by week 20, we must have our second cohort of new experiments retrospected. Or else!

We wanted to train our clients to think in milestones, rather than timelines. “We need to understand your organization’s challenges first. This will take us around 3 weeks, based on our experience. We’ll communicate if we need more time here. Or if we feel like we accomplished this in two weeks! What matters most is us reaching our milestone of understanding the organization’s challenges first. This helps us come up with the most impactful change experiments, which is Milestone # 2.”

So, milestones could be an interesting lens to plan and estimate effort from.

Next, attention.

Attention

We can also estimate based on how much we can attend to at a time.

Let’s look at two teams. Both have to ship the same seven features before the end of the year.

• Team A doesn’t work on more than two features on any given week.

• Team B works on all seven features at once.

Which team will ship the seven features before their deadline? My bet is on Team A. Why? Team A limits work in progress, which introduces focus and flow. Team B is constantly attending to tons of things at once.

I was thinking of using the word “headspace” here instead of attention. I went with attention. To me, attention is what we choose to care about now. Headspace is the finite space we fill with what we choose to care about. When we attend to something, we choose to observe. When we “have headspace” for something, we draw attention from a finite resource.

How do we estimate effort based on attention? When our attention is spread on many efforts, we increase our estimates.

This month, our team is taking on 5 efforts. Since we’re working on more at a time than what we’ve taken on in the past, I reckon we’ll need at least an extra month on our timeline to complete these efforts.

How do we decrease the amount of time it takes to complete our efforts? Bluntly, how do we move faster and get more done? Limit work in progress. If you need a starting point, attend to no more than three (mid-to-large) efforts at a time. The exact number doesn’t matter, the constraint you create is what matters more.

Okay, that’s attention.

Now, energy.

Energy

This one is the most woo-woo to me. It’s not quite quantifiable. But let’s indulge for a second. What might estimating effort based on our energy look like?

Think about when during the day you have the most energy. I have the most energy in the mornings. I plan my creative work (writing, strategizing, workshopping with others, even climbing) in the morning. I generally get more done in the morning. Others have more energy in the afternoons or evenings, so they do their creative work then.

Think about how shopping spaces see their highest sales in Q4. Holiday season!

Think about how consultancies tend to see their most work in January (applies to some, but not others, of course!). Big orgs have their Annual Plan™️ for 2023. Budgets are allocated before the end of the year to execute the plan. This is the energy that client services businesses move from.

We use our energy to move and accomplish. Yet, we rarely consider energy when planning and estimating effort. Maybe let's assume that we can get more done during high-energy seasons, and less done during low-energy seasons.

Or maybe that’s too simplistic. What if we got real nerdy about energy?

• What if we created awareness about where the organization's energy is at? I mean, burnout is real for a lot of us. Pulse check your org’s energy.

• What if we focused on efforts that give us energy and not focus on efforts that drain us?

• What is our “renewable energy” that can fuel our org to do our best work?

Again, I feel out of my league when trying to say anything that has to do with “organizational energy.” But maybe it’s a thing. There are some good thoughts on this here, here, and here.

I just know I try to dip into my own energy as fuel for what I take on. And I know good relationships energize me. Maybe there are implications to organizations here too.

Milestones, attention, and energy as ways to better estimate effort

Let’s use milestones, attention, and energy — in addition to time — to discover how we can better plan and estimate effort. Milestones, attention, and energy aren’t tangible solutions that we can act on to improve how we plan and estimate. But they are lenses that we can use to discover tangible solutions.

What are other lenses you use to estimate effort?

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What I’m Reading

1. Aaron Z Lewis’s designing time arena channel is a treasure trove.

2. Role-Based Team Structure. By Clay Parker Jones. Very clean summary.

3. Keep your experiments separate. “…sometimes, play around with implementing a feature, learn something, and then throw that code away. Try implementing it a different way—not thoroughly each time, but enough to learn something."

4. How Nike Won the Cultural Revolution. Was at the Nike Employee Store in Portland. Was pondering how Nike has masterfully appealed to niche audiences yet as a global brand.

5. Welding! Cool tool built by Hugh. You might like this if you write, don’t always love DAOs, but are curious about crypto and sharing knowledge.

6. Seen. A project by a group of East and South East Asians in the European design industry. Creative, smooth, thoughtful. Shoutouts to Ezekiel Acquino for the share.

See you in two weeks,
–tim