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Kristen DeLap

Personal lettering, professional thought leadership, community resources

August 12, 2025

Time Estimation

by Kristen DeLap


Vector illustration of birds eye view of team meeting where four people sit at a table with laptops.
Vector illustration of birds eye view of team meeting where four people sit at a table with laptops.

Estimation is becoming harder. Figuring out how long a given task might take has always been a little fraught, as many organizations have an expectation of speed, but with the advent of new AI tooling, there are more unknowns. But estimation is as important as ever in the product development process.

Estimation does three things for a team:

  1. Provides transparency

  2. Opens up a conversation

  3. Reinforces prioritization

First, providing estimates on work gives information to the team and stakeholders, making the process more transparent and generally collaborative. Your stakeholders have more realistic expectations about when a feature they’ve requested might launch. Product managers and scrum masters know when to check in with the development team without being intrusive. It removes an element of surprise from everyone.

Secondly, delivering an estimate on a piece of work begins a conversation. Questions about if elements are included or not can be answered. Information about if that fits into the timeline of the larger epic or campaign or project can be given. Complexity or dependencies can surface earlier, instead of waiting until they are more emergencies.

Third, understanding how long work might take gives clarity to how necessary the work is. For both the product team and the stakeholders, the question can then be asked, given this amount of time and effort, do we want to continue with the work as is? Or is something else best suited to begin now? Estimations can help clarify if we are on track for the goals of the product.

Estimation does not always need to be rigorous. Words like “ballpark” and “t-shirt sizing” are appropriate when talking about work to be done. Story points are more exact and often used, but also have their dissenters. The important part though is the dialogue that comes from the act of estimation and delivering that estimation to interested parties.


STAND-UP EXERCISE

In your product team, review your estimation process. Is everyone on the same page about how estimating work happens, where it is logged, and what to do when/if estimates change? Talk about examples of when presenting an estimate to a stakeholder changed the work - was it de-scoped or expanded, were complexities discovered, did the overall project take a different shape?

If you have been tracking estimation over time and have begun to use AI tooling, is that changing the way that you estimate?

For your team, when are estimates presented to stakeholders and how does that conversation emerge? Are there opportunities to improve that process and relationship?

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TAGS: Agile, product standup, metrics


June 6, 2022

Asynchronous Ways of Working

by Kristen DeLap


The most effective product teams know how and when to communicate with each other, which is why all teams should have agreed upon “ways of working”. This could be referred to as ground rules, or working agreements, or baselines, but they should define how the team wants to work together, what they want in the working environment, and what they want from each other. There are many templates out there, and perhaps we’ll revisit this broader theme in a future stand-up topic.

But I’ve recently asked my team to reconsider their ways of working in terms of the working environment. Much has changed in the last two years regarding virtual work, and our organization (which was previously quite location-specific) has hired folks from across the globe in that time. This means product teams span countries, timezones, cultures. Since some folks have begun returning to an office at least a couple days a week, and some folks won’t ever go into an office, it is an ideal time to revisit the topic.

One of the original principles of Agile was regarding physical co-location. That has obviously eased and been replaced by virtual co-location. But I asked the team to consider asynchronous communication for areas where they might never have previously thought of it. Geekbot published an article explaining how to run asynchronous stand-ups, that formerly sacred synchronous touchpoint of each product team member’s day. (Geekbot has incentive for this, as their product is a Slack plug-in to help automate/optimize this process.) Finding tools and processes that optimize for all folks on the team is necessary for an effective product team.


STAND-UP EXERCISE

Have your team review the Geekbot article “Daily Remote Standups: Video Call Downsides & How to Run Better Remote Standups in Slack”, and then discuss if they have found any of the same challenges as the article outlines. Are folks getting burned out on all the video meetings? Is the daily standup timed appropriately for all team members?

And then look to them to push it forward - how can they incorporate solutions to some of these problems? How would you test async stand-ups within your own team? Can you begin running asyc stand-ups for Summer Fridays? Or on days that are already ceremony-heavy like the end of sprints? How can you pair with your Agile coach / scrum master to experiment with this?

What are other asynchronous tools that can be employed within your product team? Are these documented in your ways of working?

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TAGS: product standup, communication, Agile