Founders / PMs / Developers / Freelancers, do you struggle with the planning fallacy ?
Hey IH,
I've been quietly working on a tool to improve my ability to accurately estimate the amount of time it takes to complete tasks or projects.
It started as a simple tool for myself, but the more I use it, the more I feel like it could be beneficial to other people / teams.
I would be grateful if you can share your input on the following questions :
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At work, do you struggle with the planning fallacy ? If so, can you describe your most recent instance of overestimated or underestimating the time it will take ?
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What kind of consequences do you usually face when you underestimate/overestimate the time it takes to complete a task / project ?
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Do you use any tools to fix the planning fallacy problem ?
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On a scale of 1 to 10, how interested would you be in trying out a new tool to help you and your team accurately estimate the amount of time it takes to complete tasks / projects ?
Any extra feedback would be appreciated.
Thank you!
From a freelancer perspective:
• I do struggle with the planning fallacy and optimism bias. Most often, that looks like underestimating how long it will take to do a task well.
• When I underestimate, I lose money. I price by project, based on how long I think the task will take me. So when I'm spending more time than expected, it's time I (a) didn't bill for and (b) could've billed for on another project. Two types of costs.
• My wonderfully nerdy husband helped me set up an equation in Google sheets. I track my estimates vs. actual time spent. And the equation helps me see, historically, how much I'm off by. In theory, this'll help me adjust quotes in the future.
• Mmm, 3. As a former project manager, I'm not sold that a tool can "fix" estimating. On teams especially, there are cultural, institutional, psychological, etc factors at play. Though I'd love to be proven wrong!
Thank you so much for the detailed answer! Do you mind if I reach out to you later on for some feedback / beta access ?
Sure :D
Could you explain what you mean by 'the planning fallacy' a little more, @EO ?
The planning fallacy, is a phenomenon in which predictions about how much time will be needed to complete a future task display an optimism bias and underestimate the time needed.
Yes indeed. Using scrum in software development task estimation, I've found collaborative estimation helps.
I've heard that everyone estimates badly, but usually estimates badly in the same way each time. Now I just think carefully about an estimate, check my understanding of the process, then double my estimate.
The biggest consequence is having to remind people who mistake estimates for promises that estimates are not promises.
Thanks for the feedback Neil!
I like the initiative you have but my personal opinion as to why this is hard to tackle and harder to put into a software (I am a lead engineer for years in multiple startups) are the following:
What I have seen, and seeing again with our current product (https://travlyng.com/) is that initially we experiment with a few people, understand the process, then lay out on Trello. But that initial experiment is almost too hard to time-estimate so we do not bother. After that is easy and a no-brainer.
Thus we do not try to fix the planning fallacy for new ideas, we just go ahead with it with time-boxed experiments and measure our results.
Thanks for sharing your perspective.
I can see how this would not necessarily be useful for initial time-boxed experiments, but what about after laying out everything on trello ? Do you set up deadlines for each task or a group of tasks ? Are those deadlines usually met ? What happens if they're not ?
Thanks again!
Once we get a hang of the new idea, then we want to put some timelines. But here we want to be as precise with the amount of work as possible because there are edge cases and people feel demotivated if they are always under-performing by some metric.
All right, thanks!
Last question : What tools do you use other than trello to set deadlines / check progress / reset timeframes ?
Hey no worries about asking questions, IH is all about discussions.
We use solely Trello at the moment, simply setting deadlines. But I would say we find multiple limitations, including better time-based planning UI.
That said, since core focus becomes actual work, we hardly spend time trying alternatives. It also becomes a pain to shift tools.
I've been estimating projects for years and I still underestimate all the time. Here's how it looks to me, for the kinds of projects and clients that I work with.
I would be reluctant to try out a new tool because the pain point doesn't feel like a lack of tools (I already feel like we have too many project management tools.) It feels like it comes from the risk and uncertainty in every project.
For me the challenge of estimate accuracy actually translates to a challenge of communication with the clients/stakeholders. Some stakeholders don't want to think about the fact that estimates have uncertainty, because they want to use the estimates to schedule the rest of the project. So somebody has to "eat" the uncertainty. We do that by giving an inflated estimate to the stakeholders, so that there's enough margin. So the correct estimate isn't one that is as accurate as possible, but it's the one that finds the right balance between having enough margin and satisfying the stakeholder's desire to see progress.
I like the concept that exists in Basecamp which they call "hill charts". It splits tasks into two phases: the "figuring it out" phase (high uncertainty and risk, hard to estimate) and the "making it happen" phase (lower uncertainty and easier to estimate). The interesting thing is that apparently the reason why clients like these charts is because they can see items moving along through chart, so they care that things are progressing even if there's no clear estimate to be given about how much time it's still going to take.
I totally get your point about having too many tools. Which is why I've been trying to find a way to integrate this with existing project management tools. Would this make you less reluctant to try it out ?
I can also see how giving stakeholders/clients an inflated estimate is probably the most sustainable way for everyone to be satisfied. But do you set deadlines internally ? Are those deadlines usually met ? Would love to hear more about your workflow internally.
Also, are you working at an agency ?
Thanks!
P.S : tried checking out Neptune PDF, I get ERR_SSL_VERSION_OR_CIPHER_MISMATCH.
hey, this sounds interesting and heaps useful. I don't have any fancy method, but simply multiply by 2.5 the time that I expect to take for it. in my case the primary problem is that there are many things to be juggling in between and the time you consider doesn't take into consideration the rest of the things.
i might be interested in the tool, but largely depending on what it offers over the table, up t this point I feel that the problem is in planning too much, overthinking stuff, rather if you try out you will be able to iterate faster, so If I wouls consider a tool, it should help me to get out of the planning and into doing the first steps as early as possible. but I reckon my case is not so common.
Thanks for sharing your experience Robert!
May I ask what you're working on ? Just so I can put your words into context.