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  • Dana Drummond

Deadline Hell: The Planning Fallacy and Optimism Bias


We kicked off the federal grant proposal six weeks before the deadline with a team meeting. During the meeting, we determined the scope of the project, drafted a preliminary budget, created a timeline and assigned tasks. According to the timeline, we would have a final draft ready a week before the deadline - with plenty of time for editing and review before uploading it four days before it was due.


I pictured myself sipping tea while I lovingly reviewed each element before carefully uploading it. If I ran into trouble, I would calmly reach out to the help desk - and they would think I was awesome because it is still several days before the deadline.


Reality: The actual proposal was frantically uploaded at 10 pm the day of the deadline - 59 minutes before the portal closed.

“NEVER AGAIN!!!!” I silently screamed to myself as I drove home, bleary-eyed and frustrated. Although the grant was funded, I can’t say it was my best work.

Confession time: During my career as a grants professional, proposals (especially federal proposals) almost never adhere to the timeline I set. Fortunately, I’m not alone.


One of my favorite podcasts is Freakonomics. I particularly enjoyed a recent episode titled, “Here’s Why All Dana’s Projects are Always Late - and What to Do About It.” Okay, it didn’t have my name in the title but it could have. The podcast discussed the very real phenomena of “The Planning Fallacy” and “Optimism Bias.” It turns out that these are real things that are studied by researchers. All this time I’ve been contributing to science!!!


According to Freakonomics, the planning fallacy is a term coined by psychologists Danny Kahneman and Amos Tversky. It stipulates that people tend to underestimate the time it will take to complete a project, knowing that similar projects have typically taken longer in the past. It’s not incompetence or dishonesty that leads us to do this: it is optimism.


Optimism bias is actually considered a healthy state of mind. Being optimistic allows people to live longer and happier lives. Without it, we would have never explored new lands, sought cures for diseases or dedicated resources to art. Optimism is a great thing - unless you’re on deadline.


Freakonomics interviewed researcher Katherine Milkman, who disclosed several causes of the planning fallacy:

  • Overconfidence - in our world, exuding confidence is rewarded. Instead of saying, “I’m not sure I can do this in the time allotted,” we stand firm in our confidence that we can do it all!

  • Coordination neglect - the more people involved in a project, the longer it takes. As a grant professional, I deal with this regularly. On large proposals, I feel like I spend more time managing what I need from which person than I do actually writing the proposal.

  • Procrastination - When I don’t start the preliminary elements of a proposal in a timely manner, it pushes everything else back. Milkman asserts the primary cause of procrastination is impulse control. We tend to do things that are instantly gratifying (knocking out a quick LOI) rather than something that is complicated, frustrating and long-term.


I would add a fourth element to the planning fallacy: something I like to call “whack-a-mole.” Because I am optimistic, I forget how many other things pop up and have to be dealt with during the time I’ve otherwise allotted to work on a large proposal. This could be anything from a sick child, an unforeseen opportunity that required a quick turnaround, or just the never-ending pings from my computer and phone.


The podcast provided fantastic context for these phenomena, how they are being addressed by business and academia, and the most promising methods of reducing errors (seriously, give it a listen). This led me to reflect on how my team and I have worked with clients to identify ways of better estimating resources and staying on schedule for grants. Here’s what we’ve found works pretty well:

  • Time tracking. At Sharpshooter, we use Harvest, one of several excellent time-tracking applications. Harvest allows us to determine how long each grant application takes for each client. When the deadline for that grant comes up the next year, we have solid data on which to estimate the amount of time it will take.

  • The Sharpshooter 90-60-30 Method. Over the years, we have developed a formal pipeline for the grant proposal development timeline. Some proposals, like federal grants, may not fit into this pipeline, but it works for about 75% of proposals we do: 90 days before deadline, we tag a project as being in the “preliminary” stage. During this time, we double-check the funder information, note any changes to the deadline or requirements, create a short report of previous activity, and create an outline of the required application elements. 60 days before deadline, a project enters the “Go/No Go” stage. We review the requirements with the client, identify the target project and amount and the clients contacts the funder (if appropriate). This allows a full month to determine if the organization really wants to pursue the opportunity or not. 30 days before deadline, a project enters the “Working” stage.

  • Calendaring: Based on how long we estimate a project will take, I don’t assume the time required will magically appear in my day. Instead, I actively block that time off on my calendar. If a proposal will take ten hours to complete, I make sure I have ten hours blocked off for it. Now, whack-a-mole will force me to make changes to the calendar, but at least I know I need to reschedule that time. When the time arrives to work on a project, I go on radio silence - ignoring the phone and email for that specific time period (which is typically only an hour or two).

  • Work-Flow Management: Because there isn’t a good grants proposal development application on the market (*yet*), Sharpshooter created a spreadsheet in the SmartSheet application to track our grant processes and workflow. It allows us to see what our deadlines are, where we are in accomplishing our goals and what’s coming up next.


Despite these strategies, we still fall victim to the planning fallacy. You see, optimism runs rampant in the nonprofit world. That optimism gives us the energy to address societal problems with limited resources. It gives us the courage to contact a funder who has already told us “no” in the past, giving them just ONE MORE CHANCE to invest in our mission. It allows us to sit at our desk far into the night, scrambling to upload a proposal moments before the deadline, knowing our chances of being funded are slim.


If you’ve ever worked for an executive director who WASN’T an optimist, you know how hard it is to keep going without deep-seated and well-supported blue-sky optimism. Having some tools on hand will help you leverage that optimism into successful grant proposals.


You can find a transcript of the podcast at the Freakonomics website. If you want to listen to the podcast itself, you can find it on your favorite platform. The episode is 45 minutes long, so block off half an hour on your calendar and give it a listen!