The problem with dropping Estimations - Product Thoughts #125

Now here’s a little insight into a very tactical experience I want to share with you from an experience I recently had with a team I’m working with. Late last year, we switched our working mode from a very traditional Scrum approach towards a bit more lightweight Kanban-ish way of working.

In that process, we also experimented with dropping estimating individual tickets. Instead, we worked with Work-in-Progress Limits for every columns and indicator how long a ticket was in a column. We still kept estimating Epics on a very high level using t-shirt sizes.

Now what we learned a couple of months into this experiment, is that it wasn’t necessarily the lack of estimated story points or time spent on an issue which became a problem.

Instead, the lack of asking the team the mystical "how long do you think this will take?" question led to a much less substantial questioning of the idea and requirements for the story. As a result, a lot of complexity behind the issue was only discovered halfway into working on the story. And the then found (additional) efforts might have led to a different prioritization of the item.

Not asking for an estimate (of whatever kind) resulted in fewer questions from the team because they didn’t have to think too "hard" about what was beyond the surface. I'm aware, that an initially articulated estimate doesn't mean that much in terms of how long it will take to build something. Instead, I'm more worried about the act of dissecting the complexity of a story in a more structured way.

So, we will think about the mechanisms of using our refinement meetings to encourage everyone to take a closer look at the issues of hand. And re-introducing some estimation might be part of this change. I'll keep you posted.

What are your experiences around dropping or changing the way you estimate backlog items? Have a great week and take care,

Tim

What I read last week

How to measure progress with outcomes

Good leaders ask their teams to deliver value. They want their teams to go beyond simply delivering stuff. Instead, they want teams to do something that creates value for the organization. But “value” is a tricky word — it’s too vague to really get people aligned. One consequence of this vagueness is that it makes it hard to track the progress of work. In my experience, this is because leaders and the folks who execute the work tend to think of value at different levels of specificity.

Product specifications: our template and process at Postmark

There is no shortage of “product spec” templates out there, so the one we use isn’t particularly groundbreaking or new, but I like it for a couple of reasons. First, we’re very serious about the “living document” nature of our template. We don’t fill out the whole thing up front, we host it in Dropbox Paper, and everyone on the team has full edit access. We truly work on it together. Second, I’ve had over 10 years to iterate on this. So yes, there are many product spec templates like it, but this one is mine. I like the focus on defining the problem, the market, the risks, and the success metrics before anything else happens. I like the modular nature of it — just use what’s applicable to the project. And I like that it’s fairly short and focuses only on what’s needed.

My Billion Dollar Mistake

Every week. Actually, it was usually daily. I would drop a bomb on someone in the company. It would be some new idea, some new direction, some new brilliant thing I came up with. Something we absolutely had to do right now. A new feature I thought would help us grow. (But really, it wouldn’t). A competitor-inspired idea. (A feature that wasn’t actually game changing). Something I had heard from an investor, advisor or friend. (And it seemed really cool at the time, I swear… but still, worthless). At best, it was an idea I had gotten from an important customer the day before.

4 Reasons Your Remote Team Needs Extra Empathy At Work

Remote work, by definition, removes the need for colleagues to be co-located in one place. This means that those small, impromptu social interactions don’t necessarily happen organically the way they would in an office kitchen or social space. These informal conversations are great ways to connect and demonstrate empathy at work, and for remote teams this process needs to be more intentional. A lack of empathy may be having a serious negative impact on your remote team, which, if not corrected, can break down team dynamics and lead to burnout, loss of productivity, and turnover. Let’s look at a few examples of remote team disparities that can lead to an unintentional lack of empathy, and how to spot these scenarios before they impact your relationships with your teammates:

Coaching Tools – The Plan

To set your expectations, product knowledge is where a new product manager spends most of her time in the onboarding process. It usually requires 2-3 months of time to ramp up, assuming she is being provided the necessary coaching, and she is aggressively focusing on this for several hours per day. But to be clear, a product manager that does not have this level of knowledge has no business serving as product manager for her team. And the responsibility for ensuring this level of competence is squarely on her manager.

How to run remote design interviews

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Find, Vet and Close the Best Product Managers

Outstanding intellectual ability and the ability to synthesize information both help a PM identify what a winning product will look like, and how it will succeed strategically in its market. Excellent communication, leadership and effectiveness within the company culture are required to articulate the vision for that product and get others excited to devote their time and energy. “I’ve never seen a truly great product manager that did not have all four qualities in the Must Have column,” Jackson says.

The Pyramid of Remote Team Communication

When your company runs on digital communication, the tools you use to connect your team become your office. Their design determines who will be involved in which discussions and who will be able to access what information. They impact your employees’ ability to focus and do their jobs. They shape your team’s culture in big ways and small. As a remote team, you have to be as intentional in choosing your digital workspaces as traditional companies are in designing their physical ones.

Product Thoughts is a weekly newsletter/digest I send out to over a thousand leaders in product, UX, and business every week. To learn more about previous editions and sign up for it, go to herbig.co/newsletter.